For one of my properties, the cleaning fee drops in off season a little bit, reflecting a reduced scope of work - namely the outdoor patios and pool.

Most properties that size are 2nd homes and often sell with furniture included, which can reduce start-up costs.No cap on STR permits in Washoe County on the Nevada side. 

Is the pool decking crumbling and need replaced with all new furniture?

For instance is buying furnitures to furnace the house consider part of normal management activities? 

For example: could you sell the furniture off (even though 0%) and buy some that is $500-$1k and pocket the difference to use for a future investment?  

It takes a lot of life experience and finesse to deal with people coping with huge life struggles.If I were young and starting out, I'd offer paid services for clean outs and basic staging/moving around furniture.

Phase 1 of my build is an outdoor beer garden so it will be seasonal and we are a few weeks out from that season.

I'm a resident of the lower Hudson Valley and have not had the chance to explore that area up there but it seems like its close to a number of nice towns like Chatham, NY and the Berkshires within 15 min, outdoor activities also abound in all seasons.

I have outdoor surveillance cameras in the front yard and back yard.

Put their furniture and appliances in another house of yours.