Having a local trusted partner to manage your investment properties is key as well. 

My client's have been happy with the draw process and response times as well.

I have been looking at sf homes with comparable SqFt to one of the units, as well as the units combined to try and get a feel for what this is worth.

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.  

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.

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....

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. 

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.

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.