Currently own my primary residence and 2 investment properties are a beach condo (short term) and single family home (long term rental).The problem is I run a successful business and have no time to do the research in new markets, deal flow, upgrades, making sure cashflow, property management, etc.I am also not a real estate professional.

Thanks, the purpose is to make it a place of business. 

I've been busy with a newborn so I kind of got lazy with a Home Depot quote.

I used all the money I made from a highschool business in ecommerce and selling basically everything I owned to rehab it. 

According to passive activity loss rules, every business is obligated to adhere to specific criteria, especially when it comes to short-term rentals.

It is in a tiny little town similar to a  downtown district where you have alot of businesses with home sprinkled within. 

If you’re not using a PM (I’d suggest getting one.) then I wonder if there aren’t business that specialize in moving out tenants.

They are usually good with their trade, but poor with their communication and with their business practices. 

According to passive activity loss rules, every business is obligated to adhere to specific criteria, especially when it comes to short-term rentals.

You can do both (though I wouldn't attempt to file business taxes myself), or you can do the bookkeeping and hire out tax prep, or you can hire out both.