Hey LT, I'm in Louisville KY about 110 miles to the south of Indianaplois. I lived in Santa Clara, in the 80's and here since the start of the 90's, and my company usually sends me to Tustin, about once a year.
Winter's - yeah, there can be snow, but usually it doesn't stick around all that long and generally not that much.
Nightlife - I'll let some of the younger board members handle that, since I'm older than dirt [:)]
Hot Women - Like anywhere else, you can find either! Hang out at the "IN" places and there will alway's be hotties. Also you are more likely to meet a hottie, that would not get all huffy about guns, since there are probably more hunters/farmers in the area and who have a father that is a gun owner.
CCW - I know Indiana has a CCW, but what you need to do, I don't have a clue about. Can't be that big of a deal to get though. Coworker of mine that lived in the Indy area at one time had a CCW. He is another, Calif transplant, btw.
Look at the pluses. Knob Creek - 120 miles to the south. Full Auto fun! Campybob's Bulletfest about 200 to the east. Castle Arms to the west. To the North......ahhhhhh.....well there is Michigan, Fishing, Hunting, etc (not flaming Mich, my home state, btw).
Guess what I am mostly saying is, the area in which you live in, no matter where, will have it's pluses and minuses. It's what you make of it.
Loved Michigan, where I grew-up, hunting, fishing, snowmobiling, lots of state game land.
Loved Calif, the weather, the beach's, Napa wine country.
Love Kentucky, Slower pace, Horses, not that crowded, Churchill Downs (yep, they have lots of my money)
my .02
Indy area guy's - over to you!