Will I regret change to 3.55s from 2.76s

Now you've gone and hurt my feelings . In a good year I may do 3000. Believe me, if I was in Southern California, it would be on the road a lot more. Illinois weather can be pretty crummy. I basically will not drive it if there is a chance for rain as I don't want to feed the rust monster and it doesn't get left unattended in a parking lot. There are just too many stupid people around where I live. Took me 12 years to redo and I want it to stay nice as long as it can. I think my insurance actually limits me to 2500 miles, although they've never checked up on me. And no, 4.56 aren't happening.
I have a 3.55 SG 3rd member for the 8 3/4 in my Duster (~400hp 360, 904, 27" tires), ran it for about a year and it was fun around town and at the drag strip but started to annoy me on the freeway. I put the 2.94 3rd member back in and prefer it this way because I like to be able to keep up with traffic and cruise at 75-80 mph to get where I wanna go. I won't be putting the 3.55s back in until I swap in a TKX 5-speed, at this point who knows when that will be so 2.94s it is.

In your case since you aren't cruising over 60 mph I think the 3.55s will be fine. I just got sick of it because I built my car more for high-speed cruising and handling than straight-line drag runs. With 1.14" torsion bars and 18" wheels my car starts to feel like it's "settling in" once above 70 mph or so and feels "in the zone" around 90 mph.
That is why I put 3:23s in my dart, allows a bit of that type of cruzing (75-80) while still has plenty of get up and go at the stoplight.