I have one property as long term rental and my husband has one long term rental and 1 STR.

As an active investor I “work” a note or “create” high yielding investments of notes, and as a passive investor I invest in my note fund and syndications under the same terms offered our investors. 

My question is should I hold the property and put a long-term tenant in the place?

I am particularly interested in purchasing my first investment property as a short-term rental (STR).After analyzing recent data from AirDNA, I have identified several promising areas: Douglas, Saugatuck, Fennville, and I am also exploring opportunities around Stevensville and New Buffalo.I understand that regulations around STRs vary widely, and I've taken the time to study city maps to identify areas where they are still permitted.

The exception would be if this was already permitted for STR - short term rentals VRBO then it might be worth it based on location.If you just want to buy a home and have a unit to help cover the mortgage I would still insist on lower price point or NO HOA to help get the total mortgage down so that the other unit covers 50% of the overall payment.  

Does anyone know if I am able to start an LLC and run short term rentals?

You also need to talk about your terms.

I'm looking at a long term appreciation, and in the interim serve as a second home / STR or even LTR.

So to start off, let me explain why I'm focusing on short term rentals also known as vacation rentals and not long term investment properties.

This one IS zoned for short-term rental.