Late fall and winter are best, but you won’t have the options you would in the early spring time.  

The tenant moved in end of last spring and had never had the furnace on.

His rent pays our property taxes, our water and sewer bills and will be paying to replace the windows in three of his rooms come springtime.

While I lived there, I painted all the walls and replaced the water heater.

@Nick Bradshaw I can't give advice for New York as I am located in Colorado Springs.

So I analyse each property individually, looking at major features like roof, heating, cooling, hot water, anything likely to break down really. 

Depending on what you qualify “upstate” as (I’m in the Syracuse area) people are always looking for vacation rentals on the water, primarily Oneida lake and Lake Ontario especially in the summer time

Getting a home certified as Healthy clean indoor air and clean water limits your liability too and increases the standard of living for tenants if they're not getting sick from indoor air pollution or lead in the Water they have the most time to work to pay us rent.

That error is low flow on the water.

So if it is leased through spring 2025 you need to provide an executed lease termination agreement.