.), and any special terms in there like required to maintain minimum heat, etc. 

I'd add index funds, reits, equity markets have benefit (and overhead) of greater regulatory oversight/compliance providing some protection/assurance for shareholders.

Huge benefit. 

HELOC are great for short term cash needs, but not good for long term cash needs. 

In terms of the building you are under contract on, is it brick or frame? 

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

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

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. 

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.  

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.