Hi, seeing this post is part of what made me decide to register after a few months lurking here, since I own a Specialized Globe Vienna 1--which would be part of the line you're inquiring about. I've been commuting on it every day for the past couple months, and it's carried me for about 500 miles. My commute's only 4 miles round-trip but I've been taking it everywhere--my longest trip on it so far has been almost 40 miles.
It was a bike I'd initially considered a non-option for me, since it looked like it'd need so much work to be completely viable for what I needed. However, after test riding a other similarly priced bikes at the store (I wanted something fairly cheap in case it got stolen), I found it to be by far the most comfortable for me. Since the series is designed for commuting, they have piles of places to attachs racks and bottle cages and fenders and my bike shop put all those on at relatively little cost. I guess the deluxe Viennas 1 or 3 come with most of this stuff already attached.
It's maybe not the lightest bike, but it's still not too bad. I always think it's heavier than it is becaues I always ride it with pretty well-loaded panniers--the few occaisions where I have them off I'm always surprised at how light it feels. I can also get it going pretty fast.
My only problem was that the stock wheels couldn't support my weight. After putting about 200 or so miles on it I started popping spokes. I'd get it repaired, then spokes'd pop again. Amazingly, my shop upgraded me to stronger double-walled rims at no charge. Seems to be doing the trick. A week or so after that my girlfriend decided she wanted to start biking too, went back to the shop, she test rode even more bikes than I did, found the Globe the most comfortable as well and got herself one too. We got her the Vienna 3, which comes with strong rims and better componentry in general. Oh, I guess I did have another problem, and that was that the pedals pretty much fell apart on me after two weeks, but I replaced 'em with some metal ones and it's much better.
You also note you prefer a more upright position--the Vienna offers that, although as my riding got strong and I wanted to go faster I found I was better off adjusting it to a higher-seat, lower-handlebar position than what the shop originally fitted me for.
I may not be any expert, but I think they're great bikes (the curving frame also gets a lot of compliments, I had a driver give me a scare once because he was trying to get a better look at it and ask me where I got it). If you're a heavier guy, I'd just not bother with the level 1s of the San Francisco or the Vienna--get something with stronger rims. I don't find the lower-end componentry on the Vienna 1 to be too much of a problem since I learned how to adjust it to where I like.
I don't know how directly similar all of these are, since I haven't gotten to know them in so much detail, but other ones we looked at were the Specialized Crosstrail and Carmel, the Giant Tran Send and the Kona Dew and Smoke.