I'm really wanting to set up a PC to play mostly older titles that I have. I love finding forgotten games or software at thrift stores and such. Obviously the biggest thing is that I no longer have a pc with Windows XP. I'm wondering if I would be able to use a virtual machine and have success with these 90s/early 2000 titles, or would it just be best to pick up an older PC with XP already installed. I would love to hook up an old CRT monitor and relive some of the old days, but I'm not sure what the best method would be. Just curious what you guys think! Thanks.

An ashtonishing lot of older games can actually be played on Windows 7, they might need some tinkering like killing the explorer process, setting single core affinity or capping the framerate to 30fps. Most info is on Google if you know what to look for.
There are only a few instances I needed to resort to XP, one was because a few Starforce protected games that didn't have cracks and the other one was for games with CD audio, XP allows for CD audiovolume control but otherwise most of these games would run on Windows 7 as well.
I've got a couple of games though that really require Windows 9x, I might try a virtual machine for those that don't need 3D accelleration, but as of now most virtualmachines don't really support Windows 9x.

I think an early Pentium 4 or AMD equivalent is what you should look for, check if you can get Windows 9x and Windows XP drivers for it though.

Yea it may just be worth it to try and just run them on newer OS. I only have PCs with Vista or 8 so I'm not sure what the compatibility is like. I know I used to have a lot of trouble with VIsta as far as running older games go.

For me atleast, I just stick to what they put on here on Good old Games. They thoughtful test (almost) everything on different OS's and let you know in the system requirements what works. Very nice indeed.

Yea I know, GoG's great. It's really introduced me to a lot of stuff. I'm mostly referring to physical discs that I have from back in the day.

You don't need a PC with Windows to emulate older console games. There are programs to emulate the most popular consoles for Mac, Linux, on mobiles(Android/iOS) and more. You didn't say what your specific platform was but if you did I could tell you what you'd need to get. :)

What about games that had issues with hardware running at a dramatically faster speed than the hardware of their time? Hitman comes to mind here.

If it's only for classic gaming then you should install XP.
Yes it's outdated and it's official support has ended but community is still working on community update of XP.

If you have a powerful machine and want to run some very old games, your best bet might be to set up a virtual machine, if they absolutely will not run in a current environment. Or if your machine is a Mac.

In some cases, a game that doesn't work on modern Windows may work in WINE.

I have been able to run Exile: Escape from the Pit on a 32-bit Debian GNU/Linux VM with WINE.

Buy a second-hand old PC with XP installed, if you really have such old games that don't work fine on your current newer PC. Of course you have to make sure the system fully works and is not about to break down. Depending on old systems is of course always a bit of a dead end, they WILL die at some point, and it will become increasingly harder to find replacement parts or PCs. For now there's abundance of suitable older PCs sold, I guess. I bought one too last year for like 20€ when I stupidly broke my similar old retro PC. No one is making new old PCs to replace those which break down.

In my experience the virtual machines (like Windows XP running inside VMWare) are not worth it for gaming purposes. Especially since you are trying to run original retail games, it is the CD copy protection that those virtual machines may have issues with. For instance, when I tried to run Wheel of Time in a VMWare session, I recall it had issues detecting the CD while playing, even though the CD was original. Apparently the CD emulation layer or whatnot of VMWare + Windows XP didn't like the copy protection used with the game, or then it was something else.

When I applied a noCD crack to that game, then I was able to play the game on that session. Kinda. It ran, but there was something wrong with the graphics (not fully sure if they were running 3D accelerated or in SW mode, it was kinda like in between), and the mouse aim was broken, making the game mostly unplayable.

I tried some other games too, e.g. the GOG versions of Gothic (unplayable IIRC, barely ran), and Gorky 17 (this actually ran playably which was nice, but only in software mode IIRC).

I really hope emulated Windows 98SE/XP/7 environments will become reality at some point, a bit like DOSBox and WinUAE. People can play old Amiga and DOS games (even with Roland MT-32 music and 3Dfx support!) without depending to the original old hardware, I wish the same sometime happens to older Windows games. I know it is far more problematic to come up with WinBox with full DirectX support and such than DOSBox, both for legal and technical reasons, but one can always dream.

Also, Linux with WINE does sound somewhat promising too, at least to get some games working. Maybe I should install Linux Mint on the side of the ASUS so that I get more experience with WINE regarding gaming. So far I've used Linux on so old PCs that it doesn't make much sense to try to find out how well Windows games run on them.

I think I don't understand the problem, I don't remember ever having issues running the first Hitman game, either on contemporary or new PC's, though it has been a few years ago since I played it.
If you mean that the game runs too fast on newer systems, try setting a framerate limit with programs like Rivatunerstatisticsserver or RadeonPro, if it has slowdowns or synching problems try setting single core affinity.
If it can't initialize 3D hardware at all maybe a glidewrapper can help out and of course try all the usual Windows compatibility settings.

Magic Carpet... x.x

So far I have only encountered one game that did not work, and that was because of 64bit windows, it was Winzer Deluxe, a 16bit application. So unless you want to play 16bit windows games I see no reason to use XP. I suppose you could also use Win7 32bit.

I think it's definitely the late 90s Windows titles, particularly ones optimized for 98 are the most difficult to run on modern systems. I figure they run best on XP, aside from 98 itself, which I just find too outdated. Granted, some of the games I've tried to play and failed are rather obscure, like Bug! from Sega. I also hate compatibility mode, it does nothing. Ever. Haha.