Personally, I started in a market close to me as I wanted to do rentals so until I got my process down, I didn't want to venture too far from home.

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

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

I just had a conversation with Property Meld, a company that focuses on maintenance.

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.

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

I wrote an Excel macro that did a CSV to IIF conversion that QB would read, and I believe there is software out there you can buy to do this, but it became cumbersome.