The majority of my career has been working in NYC and I have a bunch of connections there so I don’t see an issue with getting a new job.

On the 2 long time STRs, we have made enough over the years (income in 2019 was over 1/3 the purchase price) that having an off year is not an issue.  

I am looking for something that is user friendly, makes automated emails to tenants the day before payments are due, when they are issued a late payment fee, an eviction notice, has the best credit card processing fees and automatic payments. 

You're just trading direct-pay tenant issues for S8 issues.

In the event of any landlord/tenant issues, having an active rental license makes your life much easier.

Are you comfortable with the sargassum issue.

Account ClosedThere’s no correct answer to this, just having a discussion.There are pros and cons points and counter-points to every perspective.It appears your preference for REITs is more about liquidity issues than vetting issues, which I understand.I would suggest illiquidity can be an advantage as it prevents investors from making sudden moves when times get bad.

Cash flow issues go away and you're really just dealing with lenders to take advantage of the equity to fund more purchases. 

I've heard that some might find issue to it later so go with a warranty deed so you have Title Insurance and maintain the quality of the chain of Title...I hope this helps. 

We are in our 3rd year operating an STR and have made money every year.There is plenty of money to be made running STRs, you need to understand the market, the deals, the local issues - just like any real estate segment.Folks who think they can just buy a house in a saturated market and watch the checks roll in are going to be disappointed.