You owner occupied this condo for 2 out of 5 years? 

I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.

For example in many jurisdictions I can STR units in a duplex but cannot STR an ADU (some jurisdictions will let you STR if you owner occupy).

Britt,Just a reminder, once you rent it out and are no longer living there, the home is not owner occupied. 

On the second question, you can only qualify for 100% depreciation if it was occupied or listed for rent in December of this year.

In my opinion, the high interest rates are not as much of a problem for investors but more so for owner-occupied home buyers.

If my strategy is to have their rent pay part of the mortgage and invest in renovation in the unit i'd occupy, does this sound like a good strategy to raising the value?

The reason for it is because during pandemic/post-pandemic rush to FL, a lot of smaller investors bought condos/small multifamilies for LTR/STR purposes only without intention to ever occupy.

Winter months are definitely the most difficult months to occupy units.

Definitely loving my Toledo market 👍Just trying to get a solid B class 6 unit across the line for $160,000.Occupied but needs around $50,000 or so in rehab.Optimized will rent for $4,500+ per month and ARV will be $350,000 - $400,000Haven't found a deal like this in ages but either way you look, the numbers in the market just make sense and even with the high interest rate environment.Much success to all