And with winters shorter and not as severe thats a bonus..

Without diving deep on numbers, places like Wisconsin Dells and surrounding areas, Munising, MI for Pictured Rocks National Lakeshore, anything near Mackinaw Island - Cheboygan and Saint Ignace, lake towns near Boyne/Boyne Mountain to get some summer and winter traffic, maybe something near Arcadia Bluffs that sleeps 10-12 to host larger groups coming on a golf trip. 

-I plan on buying my first house hack in the Pinellas County area around winter time when hopefully prices drop a bit.

Quote from @Marc Winter: Just say no. 

While you're out in the field make notes of properties you like that aren't being maintained - look for high grass and weeds, broken windows or unshoveled snow in the winter.

If I had contracted out the work it would've probably cost about the same due to holding costs in the winter, time off from my job and general focus I had to put into it. 2.

I am in Minnesota where the winters are more hardcore than Philly, but you still get them. 

Four days.....in the winter, when grass down here does not grow enough to cut in two weeks. 

One thing you can do is let them mature over a a winter, wait for the spring comps to be to the books and then re-fi.

I mean Carlos, you and I have talked about seasonality affecting prices in a repeatable way (buy in Winter, sell in Spring/Summer for ~10% gains), do you see any such consideration from the Ai in it's pricing predictions below?