The short term market is seasonal.

They must give me 30 days notice, pay rent through the day of termination, pay me one month termination fee, and allow me to market/show the home during their final 30 days.

If you want to network or ask specific questions about your local market, go to your local real estate forum and connect with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking5.

If you want to network or ask specific questions about your local market, go to your local real estate forum and connect with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking5.

In my market the jump from a 2 to 3 is a big one, 3 to 4 not so much.

There's a few other things to think about too: 1 - Possible owner financing if he wants to still get a stream of income into retirement at an attractive rate compared to the rest of the market (win/win scenario, you don't need to come up with as much cash, and he makes a little $ on the %) 2 - Consider a post possession if he needs some time to move out but needs the cash up front for whatever reason 3 - Leave all the furniture/junk in the property and you'll handle clean up etc. 

@Conrado BalicustoWe utilize RentecDirect.com as a tenant facing portal to collect our rent, deposit it to our bank account, market our properties, screen our tenants, handle our accounting and more.  

I did not raise the rent last year however we did think about putting the house on the market because there are not many houses on the market for sale and house prices in this area are significantly increased.

Currently, based on a market evaluations, I have about 50k equity in the property.

I would connect with some local investor-friendly agents in your market.