Great input and stories from everyone - thanks!
Here's kind of where I stand right now. I love my Street Glide. Spent the last year and a half adding the backrest, grips, highway pegs, Sundowner seat, etc. for comfort, headlight trim ring, timer and derby covers for looks, upgraded the speakers, Clearview recurve windshield. Well, you get the idea. The biggest thing I added was the detachable king tour pack to make it into a kind of Street Glide/Electra Glide hybrid. As many warned would happen, I've hardly ever taken the tour pack off - it's too convenient for storage and way too comfy when my wife or daughter want to ride with me.
So here's the thing. If I hang on to this present bike I will want to purchase an extended warranty prior to February 2010. But now I'm hearing about Ultra Classics (2009) going out the door in the low $19's. From a cash outlay perspective, I just don't know if the resale market on my 2008 (pre frame upgrade) would get me enough money to step up to a 2009 Ultra or just a Classic for about the same as buying the extended warranty on my 2008. My brain says I'd still probably have to come up with another couple thousand but my heart says, "gotta be pretty close!"
Then there's the problem of the necessary add ons, even with the Ultra. Backrest, highway pegs, grips, a little bling. Another $500 to $1000 right there.
Oh well - noone said life's decisions would be easy! I do know I need to work hard on the advice several of you gave me - STAY OUT OF THE DEALERSHIPS!