@Matthew Rembish - I have seen very few instances where the owner was able to get full / top market value while a tenant was living in the property. Two things work against you:
1. Their showing schedule (some tenants block showings or insist on being there, which is rarely a good thing)
2. Tenants usually are living in the property in a way that their possessions and cleanliness affect the average buyer’s impression of the home (for example, misc dishes in the kitchen, pizza boxes, random clothes and boxes on the floor). They have almost 0 incentive to maintain the property in a “staged” condition. Only once have I had a tenant, and once a seller, whose house was just so beautiful and nicely staged & decorated, that it was a net positive that they were living there.
Additionally, we are going into the winter soon and a lot of people are fearing a recession. If you list now and get under contract, the home will likely sell in October or November. Yes, interest rates are increasing. If they weren’t, I’d propose maybe waiting until March to sell.
I think your best next step is sending a notice to raise rent to market 10-15% (rents went up 20% year over year) and having him choose to move out. If he stays, your cash flow is up. If he goes, you sell it. I wouldn’t list it with him in place unless he is a perfect tenant and everything is always in place. Usually you can present a property in a much better light when everything is freshly touched up (new paint, etc.) However, I will admit that sometimes it nets out nearly the same. Example: Option 1) Tenant moves out. You touch up paint, flooring, etc. Sell property for $10,000 more. Option 2) You keep tenant in place and tenant agrees to move out before the walk through at closing. You collect $2000/mo rent and don’t have to pay house utilities for 3 months ($500/mo) while property is waiting to sell and close. (((The difference may end up being negligible))).