The seasoning period doesn't have to do with how you purchased the property.

There are ways to get someone in there for the off season.

Thanks for the recommendations, my head has been buried in the sand for a bit this tax season so I haven't been on here as much. 

Keep in mind that many lenders require a seasoning period (the most common period is 3-6 months). 

Knock on wood, no problems.

With it being in the middle of tax season, I figured now would be a great time to ask since it seems like relationships with CPAs are either fantastic or awful at this point of the year.

Property specs: 920 sqft, 3 beds, 1 bath, year 1960Needs: new floors (currently Spanish Tile 12x12), full bath remodel (last updated 12 years ago, all white subway 4x6 tile), needs new roof, needs landscapingThe kitchen is about 7 years old (cherry wood cabs, black/white marble countertops), A/C 2 years old

It was a 1960s build with holes in the roof, severe mold and wood rot damage.

So one red flag I do see in your analysis is zero seasoning period.

Most banks/lenders will require an ownership seasoning period from 90 day to 6 months or longer.