I've been taking RMDs each year as required, and to think that now I am allowed to empty the remainder of the account and move it into my personal IRA without paying taxes on the distribution.....well, that seems to generouse to be true from the IRS....

I think tax benefits should be secondary to buying something that would work well as a STR.I would recommend you consult a tax professional to see what possible tax benefits you could receive from buying this STR.

Rents continue to climb as well but likely not enough to keep up with increasing monthly mortgage payments when considering interest rates and soaring property values.There are 2 main schools of thought when considering investing in an expensive market like Long Island.- Robert Kiyosaki, Grant Cardone, and similar thinkers believe its best to invest in markets with higher cashflow while renting where you want to live.

I think we want to, well, basically "torture" ChatGPT with questions.

Found T&H realty services to be pretty interesting as they provide both buyer brokerage service (to help me find deals) as well as do property management i.e. they are not full turnkey provider necessarily, but reduces some of the hassle for me I guess as an out of state investor. 

While you should always consult a CPA and/or attorney for their professional advice, here's my 3 cents (I'm sure others will chime in as well):1) Having an LLC may make it "easier" to track but it's not needed in this situation as you can run this through your personal return just as well.

I have a client in ATL that knows STR very well and could provide some resources if needed.

There's a lot to this and illinois will not approve you without these things in place, as well as some others.Good luck.

Often times they come back with a list of repairs that they would like to see to protect the home or mitigate liability. 90% of the time those items were on our list to fix anyway, and sometimes we even haven't done before we get the letter from the insurance company.

Since I have a lot of grey hair, I tell it like I see and will tell you what I think is best regardless if it falls on willing ears or deaf ears.