Waiting until Fall or Winter means you'll have fewer prospective tenants out there looking. 

And anything within a block or so of the ocean is going to take an incredible beating from the winter weather salt air etc etc.. and then you have the Tsunami that is coming with teh massive earth quake that will come and that will wipe out whole towns on the Oregon coasts.

Another example would be a tenant goes on vacation in the winter and heater breaks and freezes the pipes, because the tenant was on vacation or not home its not their fault.

Any tips you have when dealing with a tenant who consistently breaks lease, lies about property damage / repairs needed, does things like keep the heat off in the winter when shes closed for the one day a week.

My cabin is in a better location of Sugarloaf, it's walking distance to national forest, over 1k square foot home, and the lots across the street aren't developed so it feels less crowded. 

In any case, I attach below a screenshoot of the seasonality page for Fresno, CA.You can see that the demand is higher in the summer than in the winter season.

Winter occupancy rates normally dip, so the fact that you're at 85% for December says you're doing something right. 

From my experience of owning and operating 3 STR's in San Antonio, the mid term rentals have been great during the late fall and winter months, but you'll definitely want to take advantage of STR during the late spring/ summer here.

They will be forwarding over a list of contractors they use.Does anyone know what a typical contractor load-out would look like on a land development deal that will convert raw forested land into a "Ryan Homes" type subdivision? 

Quote from @Marc Winter: Why bother--just say NO!