At the end of each season I typically receive a fairly generous lump sum of cash from the players.

Could I wait a year of seasoning while renting out the home, refinance to a conventional loan with a much lower APR and pay off the investors without paying that investor or hard money loan for that entire year out of pocket?  

I would probably piggy back some on Peter's idea and cite the lack of basic building knowledge some tenants have,  with interesting examples like....pulling out a dryer to get a lost quarter but disconnecting the vent inside the wall to then vent moist air into the framing causing expensive (thousands) rot repair.putting a tarp on junk (literally) but slanting the tarp angle right into the siding in rainy season (rotting your new siding--but preserving their worn out tires).attachments to clutter, rusty junk, semi-operational cars and illogical desire to retain said junk and debris.I sort of also fall back on the divide between some of the personal management skills of landlords and tenants (realizing it may be why they are tenants, for example). 

He left the property during the slow rental season during the holidays.  

Newish washer / dryer, both high end3-season porchBig deck, nice back yard, fire pitQuiet cul-de-sac with a park at the end (very rare for the city it's in)Public transportation on the corner to just about anywhere in the metro with transfers2 - 3 minutes from multiple major highways / freewaysWalking distance (or close to it)to major mall (Southdale) and premium shopping (Galleria in Edina, MN)Potential marketing points / targets:The home is < 2 miles from the Best Buy HQ, and public transport goes straight thereAbout 10 minutes from MSP airportAbout 10 - 20 minutes from downtown Minneapolis, Mall of America, and most major concert or event venues in the city, and just a few minutes more from all of the same in Saint PaulEasy access to the west suburbs, which means access to things like Hazeltine GC (regular host to major golf tournaments, like the Ryder Cup this past year)Minnesota / Twin Cities are home to 17 Fortune 500 companies (http://www.twincities.com/2017/02/06/minnesota-has...)I totally expect making this a vacation rental to mean it will take more of my time, and not necessarily a trivial amount.

You need to build relationships with some active, seasoned investors who will help you learn from the start how to do it right and legally and by partnering you'll have an opportunity to earn a little money while getting valuable education along the way.  

How would other seasoned landlords handle this? 

I understand this is the slow season but what should I expect for a timeline to get a renter in?

If they decide to take it to small claims you will probably lose since the tenants don't control where you live or what the difference is in seasonal market value.

I have a seasonal Lakehouse rental, have been using a PM company the last couple years, as I live across the country from my rental, but have never had renters insurance.