I’ve sold 13 properties on terms.

We have been contemplating our strategy to start our business by having my sister buy her first home locally here in Connecticut, a duplex as her primary residence and live in one unit with our mother, while renting out the other unit to a resident, and be able to also rent out her single-family house as a short term/midterm rental to traveling nursers/working professionals on furnish finder.

If they continue to smoke in the apartment, you have grounds to file for eviction due to them breaking the terms of the lease.

I am looking to learn what is the best way to leverage that through LLCs to get into the multi family or long term rental investment game. 

In the next couple of years I will look at whether the long-term appreciation approach is practical.

This has been well established for a long time. 

I'm open to this but would like to charge a monthly pet fee or a one time fee (per a year long lease). 

You might also be a good candidate for a small boutique hotel, an operator looking to retire will often entertain seller financing on fair terms and you could likely qualify for a SBA loan to help with your vision. 

I heard that short term loophole is a one time benefit that you get the year you start service.

I have some good folks now but it took a very long to put a good team together.