I'm not entirely sure he will stay til the end of this new 6-month lease.I have only recently started talking to my real estate agent, and she has indicated that the best time to sell in my city's market may be sooner than the end of my tenant's lease.

It's a way to keep in front of them and stay top of mind.

And even if you start your own company it can become profitable if your able to tap the vacation and business extended stay type rentals.

Stay away from multifamily if price is cheap or sounds too good.

However, if you like the residents and want them to stay you can let them know the rents are below market and work with them to get it up.

She wants to stay and wants her sister to move in.

Go as big as I can while staying out of the commercial loans.

If none of this sounds appealing try wholesaling from a distance or working for one of the bigger wholesalers in your area to learn the ropes and add value Best not to take advice from people (especially unlicensed brokers) that either don't know or care about staying legal.

The nice thing about when they become available, the people moving out usually want to sell their appliances and furniture because they are going to a nursing home or to stay with family.Before you go overboard, make sure there is a demand for STRs in your market. 

There are many out there and I suppose some  owners are happy to  make  8 to 10K a year after  expenses and utilizing  the home for their personal vacations, but the investors getting 10%+ seem to be splitting it- one company does just the bookings for roughly 15% Commission (per night or per stay) and property manager does just Property Management.