I'm guessing this is a reference to STR/AirBnB type setups and the answer should be "No" even if I'm renting month to month so long I'm not doing short term rentals??

I would connect with some wholesalers in the area.Also, there are some alternative ways to invest in Real estate for a big return.. for example, there is a desperate need for corporate rentals (furnished short-medium term leases) that pay 3 times per month what a traditional lease would demand.

If you are thinking about a "house hacking" loan on a 1 to 4 unit place  that only requires a 3.5% down payment but try to get on  3 or 4 unit place under the same roof, which is one of the parameters of the FHA loanIf you need any short term return, you might try a Fix and Flip type with wholesaling and /or a quick flip. 

To make it short.

I have 2 houses, 2 townhouses, 1 condo that I have been renting short term with good success.

From what I experienced, when a property is sold, you're due gains tax to the federal and state authorities, either short term or long term if you're the owner.

I feel like it is worth it as I have been loaning that money out and getting a return of 12-15% but it has been just doing short term hard money loans. 

Good morning,I recently completed my last flip and I am kicking the tires whether I should just sell it or keep it as an Airbnb until I hit my year mark and 1031 it or pay long term cap gains instead of short term if I sell it then.

Always have a short contingency in your offers.

I am in the business for the long-term, not short-term gains.