For nearly half a year now, I've been struggling with the first game in the series. I've had this series for years now, up to New Vegas, but I still feel like I haven't mastered the games. I can't count how many times I've written down notes for a build, then later had to rewrite it and all the others because I came up with new ideas. Now I have a printer and can print off those sheets, but I've had to reprint some pages completely because of new ideas, such as better endgame weapons, what perks to take, etc. Other players have given me their own advice on what I need to do. I can't count how many times over the past half a year that I've deleted my character in the first game and started all over. But sometimes I feel that I have to wait a week before getting comfortable enough to try again. I have the unofficial patches for the first game, the Restoration Project for the second game, the unoffficial patch for the third game with other minor mods, and the YUP patch with other minor mods for New Vegas. I'm not adding anything unofficial because I'm a purist who wants to keep the games with their vanilla feel.

Recently, I've come up with a method to optimize SPECIAL in the games leading up to New Vegas, but not Tactics, since I still can't get the hang of that game. With this method, I can qualify for all perks without chems (save for being an idiot), get 100% critical chance with ranged builds and Sniper, have reasonable health by endgame, and get enough skill points to spread. Hand To Hand characters need to have Strength maxed by endgame for maximum damage, while maxing the stat is optional for ranged builds.

In 3, I plan to have Strength maxed endgame for all my characters regardless of whether or not they take Almost Perfect. This is due to the fact that the game allows you to carry a wider arsenal and the lack of weight for ammo. I feel that this is necessary so that you will be able to handle any opposition. For example, using a Gatling Laser when up against Super Mutant Overlords, Masters, Behemoths, Albino Scorpions, and Reavers. Higher to max Endurance by endgame is better in my opinion for Low Critical builds or critical builds not using VATS due to the damage they take in VATS being reduced. Only the critical build attacking primarily out of stealth will have Luck maxed by endgame if not taking Almost Perfect. The assassin, which attacks primarily from stealth, doesn't need max Luck.

In New Vegas, all my builds will have about 7 or 8 Endurance so they can get more implants. All ranged chracters will have Agility maxed by endgame to take advantage of the increased reload speed. All builds using criticals (except for those using automatics) will have Luck maxed by endgame. Builds focused on getting as many critical hits and inflicting as much damage as possible get Voracious Reader and Comprehension.

Put simply, I'm a perfectionist. I don't want to feel that I'm wasting skill points or feel that my initial SPECIAL could have been set differently. In recent playthroughs, I've tried starting with low Perception to qualify for Sniper with mentats and the implant, I've tried starting with 9 Perception, and tried also starting with higher Endurance for ranged builds. All of them got deleted before finishing the game as I felt I was wasting points that could have been spent or set better elsewhere. For example, investing a few points into skills such as Barter, Sneak, or Throwing. I've also carefully picked out endgame weapons for each of my builds to use both a one handed weapon and a two handed weapon, unless I've taken One Hander, in which one of them is better for all purpose and the other for when I need more damage. In the second game, I make sure to include one weapon that can reasonably damage the final boss since I don't like to have to depend on the turrets to take him down.

What I want to know is if I am doing something wrong? What is my greatest problem when playing these games?

I think you answered your question in this very post - you're a perfectionist, and it seems a blessing and a curse at the same time, I guess. Your posts are full of detail and insight that I usually don't think of when playing these games, so it's a pleasure to read them.

I think neither of Fallout games were designed with perfect/most optimal build in mind, so this might be one of the reasons why you have issues with trying some builds and abandoning them.

I admire your approach, but personally when I play Fallout, I first imagine what my character would be like: a lone wolf wandering through the wasteland for example and then I apply the stats to reflect my vision of the character. Having played pen and paper RPGs I believe that both strengths and weaknesses add to a character.

Perhaps playing sub-optimal builds would be an interesting challenge?

There's no reason to make a min/max build for the 1st 2 Fallouts. You can finish them with a less then optimal build.
There are ways to increase your SPECIAL in game, with drugs (temporarily), implants, armor and perks. Though that last option is a waste of a perk IMO.
You could use the Gifted trait for a +1 to all SPECIAL.
Personally when I play F1 or F2 I think of the kind of the weapon type I want to use and build my character around that.
The rest is mostly roleplay. Playing smart or stupid, good or bad, substance abuser or my body is my temple, diplomat or anti social, techie or 2 left hands, ... Some combos made sense to me. For instance a sniper uses a 2-handed weapon, needs to focus for a long time and in general is a support role, so doc/medic skills makes sense for such a character. A stupid charachter with melee weapons might be anti social, therefore avoiding societies resulting in high outdoorsman, low speech and barter, ...

SPOILER ALERT:
For everything you need to know about F1 and F2, you can read Per Jorner's guides:
[url=https://fallout.fandom.com/wiki/User:Porter21/The_Nearly_Ultimate_Fallout_Guide]https://fallout.fandom.com/wiki/User:Porter21/The_Nearly_Ultimate_Fallout_Guide[/url]
[url=https://fallout.fandom.com/wiki/User:Porter21/The_Nearly_Ultimate_Fallout_2_Guide]https://fallout.fandom.com/wiki/User:Porter21/The_Nearly_Ultimate_Fallout_2_Guide[/url]
Edit: my apologies for the way the links are posted, but the forum can't seem to handle them.

Tactics is 1 I finished long ago and haven't played since. From memory I tried to have a balanced team with essential skills covered.

F3 was broken if you chose a stealth character with a dart gun.

In the past, I have always taken Gifted with my characters, unless they were Stupid.

Here are some things I learned from previous recent attempts over the past few years in the first game:

-Small Frame is not recommended if using Big Guns and other heavy weaponry.
-High Endurance is only useful if fighting Hand To Hand or if going solo in the second game.
-At high levels, the difference between accuracy between what you need for Sniper and 10 Perception is marginal at best, even if using aimed shots.
-Starting with average Perception if you plan to use chems to qualify for Sniper together with the implant is not recommended as your starting accuracy is much lower and you need more skill points to have 95% chance to hit, especially with aimed hits.
-Points invested in Throwing, Sneak, Barter, and many of the other non-combat skills that cannot be raised with books are basically wasted. Why invest in Barter when you can just lower the difficulty before you shop?
-Points invested into Small Guns before raising it to max with books could be called 'wasted'.

I'm the kind of guy who doesn't like to depend on chems to qualify for perks because doing so would gimp your character in the long run. For me, It's better to have Agility maxed by the end of the game through hard points instead of temporary points gained from Psycho.

Small Frame is only taken for the extra SPECIAL point. The lower carry weight is an annoyance during the early stages of the game.
Even when going solo EN 4 is enough in F2. For RP purposes an HtH or melee build could use more.
For a sniper PE 6 or 7 is enough at character creation. You won't be using a sniper rifle in the early stages, but most likely a 10mm pistol or SMG. Smaller distance requires less skill.
Lockpick and speech are essential none-combat and none-skillbook skills. Personally I prefer to also raise the doctor skill, usually to 50. It also depends a bit on what I'm roleplaying. If it's a sniper/support character, doc skill goes to 100-125.
The first few levels you can save up skill points before getting books or use them in none-skillbook skills. An IN6 character usually has enough skillpoints endgame to not have wasted them if you raise skillbook skills before getting enough skillbooks.

I also like to carry more than one weapon endgame. A pistol helps with ammo conservation purposes against opposition, especially when using burst fire mode only weapons. Even if I'm using a very powerful rifle for the toughest foes, a secondary rifle with longer range is useful for picking off or damaging foes from a longer distance.

Here's an example of what I have optimized for SPECIAL optimization. This is for a Sniper in Fallout 1 with Small Frame and without Gifted or Stupid:

S-5
P-7
E-3
C-1
I-7
A-8
L-9

With Gifted:

S-6
P-7
E-6
C-1
I-9
A-8
L-9

WIth Stupid:

S-6
P-7
E-6
C-1
I-3
A-8
L-9

Endgame weapons are Sniper Rifle, Turbo Plasma Rifle, and .223 Pistol.

My bad.
I forgot about the difference between Fallout and Fonline (MMORPG) in which SF does less damage and i mostly use for causing broken limbs and blindeness.

I can only speak to NV since I have hundreds of hours into it. (Mostly not on PC)

If you don't mind wasting 10 perks out of 25 max, get all the SPECIAL Training.

You have to start with 10 INT. I would also hit END up because of implants. Also having more health is a must. Everything else matters little. You can still hit people even without the STR requirements being met. CHR is NBD. AGI takes some getting used to being slow, but its workable. If you anger the NCR or CL their Assassins are just walking free money. Don't be afraid to steal things once in ahwile, if you are doing a good Karma run just go kill Fiends to get it back up.

Don't haul around useless junk and you won't miss the carry weight. Take Rex/EDE and a human around as pack mules. Weight to value ratios people. PPAP. Pick up all pencils (and weightless items with value.)

If all you use is a Super Sledge, sell all your ammo. Many people forget or don't do this.

PER is annoying to not have near max because of some DLC PER checks. Clever Mentat combos may get around this.

Focus on gatekeeper skills before combat skills. I would do lockpick and science first, tag those two and speech or barter.
Take the trait skilled for the +5. EXP comes easy enough. Take the trait Small Frame for the extra 1 AGL.
NEVER take 4 eyes. The PER bonus might seem nice, but you really want the Rebreather in the eye slot for the extra DR.

DLCS-
Try to do Lonesome Road as soon as possible to get the free +1 to any SPECIAL.
OWB also has some neat SPECIAL boosts.
HH not as important.
Dead Money- Get 100 Stealth and/or a stealth boy and get all the loot snuck out and you will never have money problems again (there are YT tuts for this) No need to have a high LCK. Just play blackjack and save scum to get enough winnings for the Sierra Madre Voucher.

^My tips, sorry for the mess
***Edit, note you CANNOT max SPECIAL in FONV. Very close though. Skills you can quite easily max with 10 INT to start, especially with skill books and that perk that adds +1 to skill books. Also get that LVL 4 Perk right away at LVL 4 that adds a few skill points to each LVLUP.