Necro! I could not resist resurrecting this good thread because I am in a similar place right now that just lead me to explore the posts on this forum. When it was new, I played Ultima VII The Black Gate and it was my first time playing an RPG. It was such an amazing experience. I just loved every moment of it at the time. I've had fond memories of the game ever since. I never did play Serpent Isle for some reason. I have no idea why all these years later but I did go on to play Ultima VIII and I enjoyed that one too. I also played Underworld I. I wanted to play Ultima IX when it came out but my hardware like many people's then, just couldn't run it. I never did get back to it either so I am hoping GOG will release VIII and IX sometime soon as I'd buy them both in a heartbeat.
More on topic though, I bought all the Ultimas available here on GOG with the intention of playing through the entire series in order. I expected the early games to be crude and sure enough they are. The thing is, there really isn't much story to 1 through 3 to compel me to slog through them. Just for fun I did install them and I did play a little of Ultima I up to the point where I'd met Lord British, gotten a quest and also explored the nearest dungeon some. It was fun to see what it was like back then but I didn't really feel like playing through the whole thing given the very simple story to it. I got the same basic feeling about Ultima II and III as well. All three seem pretty similar to me in their simplicity and very simple story lines.
The funny thing is though, I feel a certain sense of strange guilt along with a strange compulsion to make myself slog through the first 3 because I consider myself an Ultima fan and it doesn't seem quite right to skip anything if that makes any sense.
That was a few weeks ago. Today I installed the Ultima 4 thru 6 package from GOG, read the manual and reference card for Ultima IV and fired up the game. I know this one has some story to it at last and while the graphics remain pretty crude they are at least somewhat colorful. This being where you become the Avatar seems to me to be the real kick off to what I consider Ultima to be. Since they were installed, I took a look at V and VI just to see them. I can see some nice graphics improvements, especially with VI which is kind of exciting.
Anyway, forgive my rambling please. I'm not sure if I want to make myself do the first three Ultimas or not. I'm not even sure about the next 3 but maybe. Part of me thinks I'd have the most fun diving in where I left off but starting with a replay of Ultima VII The Black Gate, then maybe Underworld 1, then Serpent Isle, then Underworld II, then hope like hell GOG has released VIII and IX by then! That's a hell of a lot of gaming right there really and I have an amazing backlog as it is.
It's funny how I'll sweat over stuff like this while meantime I own stuff like Dragon Age and The Witcher and haven't played them yet. I worry playing newer games will really spoil me and I will miss out on the great oldies like these if I don't play them first.