You also need to build in 5% CapEx expenses for long-term big expenditures like roof, furnace, water heater.

So I hired a contractor to come clean the 40' long 10" diamater tree branch off the roof and numerous other branches leaning collapsed fences, I hired another contractor to come fix the roof leak. 

Guy wont budge on his roof.

As noted you will want a full inspection done on the following: roof, sewer lines (scoped by a licensed specialist), lead paint check (specialist), test for asbestos if you have popcorn ceilings.

It needs a new roof, new driveway, new boilers, new HVAC, and every unit needs work to get them up to code.

If you winterize properly there is no risk of future dmages in regards to plumbing and whatnot...Only issue may be ice dams in gutters which could lead to possible roof damge...You should be totally fine though

@John LeavelleThanks John, I literally just put a couple numbers in that were low because I've completely made the property new from the roof all the way to the exterior siding, paint, unit 1 & 2 now have new carpet, cabinets, granite counter tops and tile flooring.

The good:  new electrical panel, new roof, new windows.The bad: everything else. 

Originally, my rehab budget was about $63000 which included roof, siding, total redo on the inside, new furnace, air, and duct work (currently has old boiler system and no duct work) I had several companies say they wont do loans for less than $75000, so i increased my budget, opting for higher end counters, etc...

If you have not done so already it will very soon need a new roof.