When I purchased the house, the second unit was already occupied, and I decided to keep the tenant.The tenant has been living there for the past 3 years and had not missed a rent payment until a few months ago.

For your first deal, I'd look at an owner occupied property.

I'm not too familiar with your market, but i was in a similar situation in the DC metro and pivoted from renting/leasing to rent-to-own (lease option).i got the place occupied in no time with above market rent, passed on any trivial repairs to the tenants, and collected a significant option fee.The option fee is magical!

Mid term is about 85% occupied.

@Chris Villegas After losing out on many tenants due to showing a unit that was occupied or under renovation I never advertise any more until the unit is empty and ready to go.

You need your tax returns completed to get the best loans, especially traditional loans like an FHA or owner occupied loan.

Additionally, there is usually a document in the loan doc set that has you certifying that no family members would be occupying the subject property. 

It's not at all normal that commercial mortgages have lower rates than owner occupied single family homes... we shall see how long that lasts for.

I am too busy to hear about the latest unit that got broken into and stripped.. or the latest drama of tenant who cant or wont pay either their total rent or their portion of the rent after the section 8 payment. and then the constant turn over and cost associated with turnover.. the Investors buying these are not C and D class folks like the tenants that are going to occupy their props so they really have very little clue about how those folks live their life and on the razor sharp edge they are financially.

And some are reasonable at both of these things, but can't handle owner-occupied units, or multiple ownership structures, or lack the flexibility to track a real-estate related side hustle.