I've just moved here and had done a lot of research in the last some 2 yrs now and this is the place to be. (Yes, my opinion-chuckle).
Now for your questions:
First: It took me literally 5 or 6 realtors before I found a fantatic one right in lexington. He actually returns phone calls, answers ALL my questions, showed me ONLY what I wanted and even helped with my settling in(ex:hse taxes car reg and tax, license, etc. even went with me to do everything I needed to do!). If you'd like, pm me and I'll be more than happy to share

Ironicaly found him THRU someone on here that moved from up north a few months back. This site is wonderful! Great people
Second: A gallon of gas goes for around 2.89, I'm sure you could get cheaper as you scout around. This is just what I've seen so far.
Third: A gallon of milk(OUCH) Piggly Wiggly $5. and change! Haven't gone back there. There's a Walmart superstore on 378 and they are cheaper, 4. something. I also joined sam's club out on Harbison blvd.(20 to 26 to Harbison blvd.) BTW: Harbison Blvd.(my opinion) is the place to go for furniture, Columbiana mall (Sears, JC Penny), Best Buy, Office Depot, Walmart(also on 378 so, you know) From what I've been told "Publix" for meat(378), veggies and fruit. Walmart for the usual food shopping and Sam's Club(Harbison blvd.) for the bulky items we all go thru

Just a matter where you go I'm sure.
Fourth: Bread: "Merita bread" is 2.39 at Walmart. (i'm used to paying 1.30 where I used to live) so, this is a jump.
Fifth: My opinion with the hurricane thing, I too was concerned with this. We're north-west of say Myrtle beach and inland so, I dont think this is a factor. If thinking of closer to water, yes I'd be concerned. Lexington is 2.5 hours away from Myrtle and about the same to Greenville (mountain area) so, this is the midlands as SC says. Right in the middle of it all

I'm sure Lex has storms but, I dont' believe anything to be concerned about.
When you come back for a visit check out "O'Charlies" on 378 next to "Ryan's" (Ryan's also good if you like all you can eat places). O'Chalies is a nice restaurant with good food with good prices-try the (I think it's the )"New Orleans steak" It's really good

If you like fast food or dont' have the time, try "Gaxbys" have good chicken sandwiches-very tasty.
I HAVE to impress on anyone who's thinking of moving here, It IS cheaper to live here even with food price changes from where you come from. Housing and taxes are everyone's big factor and housing and taxes here are (with ALL due respect) a joke compared to where I'm from! My taxes are literally 14,000.00 CHEAPER here than where I was. YES, 14k cheaper! and have the same property and same amount of bedrooms. So, for me, it's much better. Car insurance is cheaper as well. Schools that are in Lexington 1 are really great from what I hear-you'd have to ask someone with kids about that. From what I understand they are blue ribbon schools-another plus for the area. And again, people have been more than kind here.
I hope you journey out and scout around a bit and find what you're looking for. Where are you coming from? It's scary making "the" move. But it really has been the best thing I've done if this helps any. People have been very nice and welcoming, the only people that don't seem to be that friendly are the Time Warner Cable company in town. But, personally I have yet to talk with anyone from
any cable company that is nice and helpful. So, that's a wash(chuckle).
I hope I've answered some of your questions and like said, anymore, just pm me.
Happy trails.