It's hot heck at the moment around 100 degrees, but I'm hoping it'll be worth the investment come winter time.

A common serious issue would be no heat in winter time.

I could see in NJ where you would want to because the winter time is dead.

I.e New roof Central ac for two unitsNew kitchen and bath both units New electrical (old outdated)Front and rear porches need to be redoneNew plumbing (frozen pipes) house wasn’t winterized New drywall Can reuse most of the windows just new screens Security system and cameras New lightning (flush lighting) New roof on the garage and garage doors (possibly insulate) for winter time want to add a 1/2 bath to the first floors of each unit (More rental appeal 3bd 1bth vs 3bd 1.5 bath) Siding And paint Had ideas since it’ll be home of doing spray insulting to the attic  (livable space)  (save on heating and cooling cost long term)  So as you are networking get referrals for as many contractors as you can.

Outside of real estate, I enjoy skiing in wintertime, basketball all other times and having fun with friends and family all aboard this crazy ride. 

She set it down to 50 because she thought it will cold down faster :)  Winter time - called me and said the furnace is not working and she is freezing.

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

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.

Its still on the market, winter time.

Winter time is a difficult time to rent or people to move with snow and ice unless they really have to move.