Ultima 2 is easily the hardest to get into, because it seemed very random. Of course time travel and wizards does that. Ultima 4 is the first game that really is what Ultima is. Before that is a sort of a collection of games they decided to try and tie into a single story line. If you can't bring yourself to get through all of them, start with 4. I always had a soft spot for 3, because it was pretty much all about exploration, but to get the Ultima experience, you can skip right to 4.
Also,
Matt... You should try and get an interview with Felicia Day... I know it's a long shot, but she was part of the UDIC (Ultima Dragons Internet Chapter) long... long... long ago. It would be interesting to see her take on gaming over the years, beyond just talk about 'the Guild'.
Couple thoughts:
Ultima 2 is easily the hardest to get into, because it seemed very random. Of course time travel and wizards does that. Ultima 4 is the first game that really is what Ultima is. Before that is a sort of a collection of games they decided to try and tie into a single story line. If you can't bring yourself to get through all of them, start with 4. I always had a soft spot for 3, because it was pretty much all about exploration, but to get the Ultima experience, you can skip right to 4.
Also,
Matt... You should try and get an interview with Felicia Day... I know it's a long shot, but she was part of the UDIC (Ultima Dragons Internet Chapter) long... long... long ago. It would be interesting to see her take on gaming over the years, beyond just talk about 'the Guild'.