Last year I pretty much retired. I have been looking for a place to relocate to out of the toilet bowl I now live in, and have all my life.
Kentucky and Tennessee have been high on the list as more temperate than Chicago.And still reasonably close to relatives.
I have been concentrating on Lake Cumberland in the Kentucky area and the Vonore Tennessee area.
This is not hard and fast just a starting point to look. Large acreage was my first priority but smaller land area would be acceptable if on water.

Is there a
"better" state as far as retirement benefits and tax advantages between the two?
How about firearms?
Climate?
Thanks for the advice.

I've lived in both states, close to where you are looking and you will be upgrading whichever one you end up choosing. (My wife and her family are from outside of Chicago).

I am close to the border and could live in either state and I currently live in TN. Given what you are looking for, I would lean toward TN. You can find a place on the lake and still be close enough to civilization to enjoy solitude when you want it and a nice restaurant or good healthcare when you need or want it.

Lake Cumberland is nice, but you will be isolated and there really is not that much in Somerset. I lived in Corbin for several years. In Vonore or any of the lakes or rivers close to Knoxville you will be much closer to 'civilization'.

No income tax in TN, things like vehicle registration is much cheaper, gun laws are great in either state, sales tax is cheaper in KY.

Anything specific just let me know, we live about 30 miles north of Knoxville, on Norris Lake. Tons of retirees and folks from Ohio/Michigan in our area.

**Edited to add**
To answer your questions:
No income taxes in TN
Firearms: I'd call it a draw, both are excellent.
Climate: You'll typically get a day or two more snow days in KY, but it's close enough to be a wash. Nothing like you are used to getting!

I live north of the Vonore/Tellico Lake area. Not a bad place to be. I have no KY experience other than driving through, so can't really compare. TN does tax some investment type gains and interest, etc but not income from salary.

You'll be close enough to Maryville for medical stuff and Knoxville is just another 20 minutes up the road from Maryville.

the fishing is good. All four seasons get represented well enough. Either place you mentioned will definitely be "country" as far as the locals are concerned, but Tellico Village is near Vonore and it is full of retired people from all over the country and/or well payed people like engineers and doctors and such - so you could feasibly hook up with either class of folks you like OR just stay isolated on your acreage and likely not be bothered by anyone except the meter reader or the UPS guy.

I frequently hear the real estate ads on Sirius XM advertising lake lots in TN. Are those a total scam selling swampland, or are they legitimate?

While no income tax in TN is nice sales tax can be around 10% depending upon local taxes. So dependent upon your retirement income can make a bit of a difference.
My 2nd property is 3 miles from Tenn and about 35 from Somerset Ky. I do my best to bring everything I need or stop in Somerset or Williamsburg on my way down. I cringe a bit when I have to jump across the line to grab something quickly.

I really enjoy living in Ky.
Guns are not uncommon and our laws here are about as loose as you can get and likely will stay that way as state law forbids local municipalities from creating and local gun legislation.

Somerset has everything you need for pretty much daily living. Some things you’ll mosey on up to Lexington for.
It is not a bad drive can be a little slow when the Ohio Navy is rolling deep to or from the Lake

I fled San Francisco for Lexington, KY 25 years ago. Lexington got a little too congested for us, so I retired again and we moved to Georgetown. It's 20 minutes from a major metro area, plenty of farms and acreage around the area and reasonably priced. No state income tax on retirement income. Sales tax is 6 percent, except in G-Town its 13 percent for liquor so we drive to town once in a while for a couple of bottles. There are a goodly number of gun stores, and a nice indoor range at Bud's in Lexington (yeah, that Bud's.) There is an area called Land Between the Lakes in Western KY, about two hours from here. It's got, oddly enough, several lakes and a river. Paducah is nearby and they have a lot of support industry, such as medical stuff, and they kind of cater to retirees. If you want more detailed info send me a PM, and if you decide to scout the area out drop me a line. We can do dinner or something.

This site will give you some idea of what is available and price. Don't go into sticker shock, I think they list the most expensive first. They do have some helpful filters.

www.unitedcountry.com

My buddy retired to Signal Mountain, Tennessee and loves it. He can take a short drive down the mountain to Chattanooga, with lots to do, and be back home away from the hustle and bustle in minutes.

Kentucky constitionally guarantees the right to bear arms (Section 1, para 7). I like that guarantee. I don’t recall if TN had the same constitutional provision.

Both states will be hot and humid in the summer. I’m in central KY and we seldom get extreme weather, fires, etc.

Politics are an unusual mix, where the state typically votes republican nationally, but tends to have a democratic governor. Our current gov is the exception.

I’ve lived in both states, and would be happy in either. Retirement income is not taxed in KY so that negates the income tax disparity with TN.

You’ll enjoy whichever one you choose.

Kentucky resident here. I have to echo what the others have said. Extremely pro-gun. State democrats as a whole tend to lean way further right than national republicans. Yeah, we’ve got our shitheads, but for the most part even with a dem governor anytime gun control “compromise” comes up, you get a pro-gun bill passed and signed by the governor that bitch slaps the gun control groups.

It’s hot and humid during the summer, and in the winter it is generally mild.

It’s an interesting state, er, Commonwealth. The state police here is the deciding factor that keeps protests from blocking roads, and keeps them from committing general nonsense. Even if a liberal mayor allows protestors “room to destroy” he doesn’t control the state police and the commissioner will tell the mayor to screw off. Law enforcement is generally very professional here. Some agencies are very small and backwards. But, as a whole most are professional.

If you find yourself settling here in the western end of the state, I have a standing offer to SF members that I ll do your CCDW training for free.

The Land Between the Lakes area has a lot to offer with both Kentucky Lake and Barkley Lake being premium.

I could add much good to say of the State of Kentucky. You are free here. Auto insurence is kind of high. I havn't got the chance to visit much of Kentucky as I got sort of stuck here too close to Ohio. 2 Years living in a car now and its beginning to take a tole on my health. You in retirement would love this little state. My oppinion, its beautiful from end to end.

Southern Indiana is about the same as Kentucky, maybe a little cheaper. I was born in Somerset and still have ties there but have lived in S Indiana suburb of Louisville since I was 4 years old in 1955.

Hoosier National Forest and Patoka Lake are great, cheap rural areas. Orange County & Crawford County are areas where your money goes a long way.

Indiana has great gun laws and our carry permits are good for life if you want to pay a little extra.

Tennessee

1) I think the tax thing tilts slightly towards Tn.
2) I think KY gets a slight edge on gun laws
3) whichever state you end up in the closer you are to Paducah the cheaper your overall Opspec classes will cost.

If you are a duck hunter Paducah is a great place to be. Nashville has a great airport.

I could be happy living in either, but the recently passed taxes in KY tipped the scales.

As a retiree, you'll be better off in TN.

Best wishes for a happy retirement.