You will have to pay higher personal income tax rate, versus waitingtill after one year for lower Capital gain tax rates.

So why is the $2,500mnth person paying $250 and the other one paying $350 ??????

As long as no “healthcare” services are provided (like medication or personal care), it’s not regulated by the Department of Health.

Other CPAs and firms have quoted me 5k-10k+ but are no where near as responsive and personable as my current CPA and accountant.

The owner was motivated due to personal circumstances and wanted to avoid the hassle of listing the property publicly.

I do not know that if someone is in the hospital you can force them to close, I am not an attorney, but I doubt any court will find in your favor, closings do not always happen exactly on the day that is planned, even if everyone is healthy and well, the wholesaler here is not the reason for the delay so I am not sure what exactly you can sue him/her for, they are also being held up due to the seller not being wellJust give the person some time to get out of the hospital, closing will probably not happen the very next day either, this is really extenuating circumstance. 

The idea of debt-free is that if a person is going to retire and has to completely depend on the income, they don't want a severe recession surprising them and causing them to default on the debt and losing the properties.In a normal world, I would do that as well.

I personally don't like getting a lot of automated messages when I rent a STR, I'd rather have some more personal contact.....

This is so I know if I should keep the person I currently have.

That's a great person to start with!