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

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? 

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.

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

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. 

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.

Did a "hard money loan" with family using gift tax exemption and trust as collateral (despite what Dave Ramsey says, my father and I have an incredibly strong investing and personal relationship).

However, I've been having difficulty renting one of the rooms because I've noticed some of the potential renters are either super particular, end up wanting to live on their own or with one other person (I have one room currently rented), flake, or come up with an excuses for not meeting with me. 

My best connections and referrals here in Florida have come from in-person networking events.