I grew up in Upstate NY, went to college in Daytona Beach, FL, got my first job out of college in Fort Worth, TX, had a 1 year work assignment in Wichita, KS and then moved to Bend, OR where I currently reside.
Here are my feelings on each place:
Upstate, NY: Taxes are crazy, summers are muggy, winters are harsh/long and VERY SNOWY. Everything seems like it's getting run down, not improving. Maybe that's just because I grew up there though, people tend to see more of the flaws of where they're from than other places, I think.
Daytona Beach, FL: Very touristy, hot and HUMID. I got the feeling that a lot of people with not a lot of great things going on in their lives move to FL because "My life sucks anyways, might as well live some place awesome, like FL, and be a beach bum!" Then they continue doing nothing with their lives, but at least the weather's good (in their opinion). That and the stereotypical older retirees and all they bring to the table.
Fort Worth, TX: I thoroughly enjoyed living in TX and miss my friends all the time. It was a great place to make a lot of $ and have low expenses. The weather is VERY HOT in north central TX but not as humid as FL so I was not so bothered by that much as I was working like crazy. Outdoor activities are very limited much of the year though. If you like being out in nature, it is not for you. I really liked being in a large metroplex area and all of the things there are to do there. I still wouldn't move back though because...
I love Bend, OR: The weather is the best of any place I've ever lived. We are on the east side of the Cascade mountain range, which is high desert climate, over 300 days of sunshine a year and nice and dry. Summer temps are mid eighties to nineties with lows in the 40's - 50's. So every day starts off nice and cool and gets nice and warm. We have a/c but I never turn it on because we have our windows open all the time except the rare 95 degree plus day. Winters are typically highs around 30-40 with many 50 degree days mixed in. Nights are cooler as well, but you know, you're sleeping. When it snows, it sticks around for a few days in town and then generally melts. If you want snow though, you can drive 20 minutes up the road to the mountains and ski, showshoe, etc to your heart's content any time from about November to May (sometimes more). Spring and Fall seem to go on forever (which I love). Hiking and biking are also huge here as well as family friendly, festivals, outdoor concerts (free) an rivers and lakes for kayaking, SUP, fishing, camping, etc. It's super family friendly and about 80,000 residents so a small city that feels more like a small town a lot of the time. It's the only city for the region so there's good medical care and seriously, everyone loves living here. Housing is the only downside that gets regularly complained about because it is in a serious boom right now as the local (tourism based) economy crashed super hard in 2008 and has roared back with a vengeance. We were lucky enough to buy right before the upturn in 2012 so this hasn't been a huge factor for us.
I realize I didn't give Wichita, KS much attention as my time there was short but I'd say it's a smaller version of Fort Worth with more humidity in the summer (and WIND) and awful winters (again, THE WIND). No best of any worlds, really. It's pretty small and kind of an up and coming city and I enjoyed living there in the Old Town area where we could walk to restaurants, movie theater (The Warren!) and bars. I could live there for a while and be pretty happy but it's not my first (or second) choice. Cheap place to live and pile up the stache :).
Good luck!