Even my local to me clients - 95% of them we never meet in person each year.  

That means more expensive and less profitable and, personally, I wouldn't invest there because of the sargassum issue but you might care less about it because of the lifestyle component in your case.4.

LLC, S-Corp, etc) that files a tax return or do you own it in your personal name and report rental income on IRS Schedule E? 

My properties are in Brentwood, used to be able to get many applicants, but now it's just a trickle in the height of summer and quality of tenants is less than desirable and with much longer DOM. 

Suburbs are definitely desirable.

You got bad advice from your prior accountant.You received rental income and it should have been reported.it seems like maybe he was lazy and/or doesn't understand rental concepts.The only exception is if he is paying 'under-market' for rent in which case the property would be considered personal use.I would fix the issue and charge him market rent. 

How would you fund this if you are working with less than 20k personal funds.

What does that have to do with a personal refi loan in my name?

I do agree that you need to go in person to see what is going on.

I have a Series LLC I use to collect income for my consulting business, but the income goes to my personal checking account.