We found out that there was no insulation in the walls, one of the tenants decided to open it up for us in a brawl he had with his "girlfriend". 

Each rental shop will be 1,200 square feet, insulated, have one water spigot, and minor electrical.

One of the BP members mentioned creating an LLC and PO Box to preserve anonymity - that's a good idea too in that it insulates you from any unwanted visitors. 

I was able to fund a complete bathroom renovation, brand new plumbing, new flooring throughout, new drywall & insulation, and upgrades to the kitchen, but I struggled to find consistent contractors to finish the house.

I make a plan for my week: Monday - go to HD after work and get supplies for project ATuesday - go to Property 1 after work and do project A; if raining, go to Property 2 and do project Betc...Here's a sample of my list: PRIORITY TASK UNIT TOOLS NEEDED CONCERN FALL 2019 install spark igniter 1R 1R 1.5 recoat flat part of roof EX 1.7 insulate/brick over AUX BS windows AUX BS with Eli 2 parge W wall of basement BS with Eli 2.5 brick over front 2 basement windows BS with Eli 3 remove plants on side of garage wall GAR weathering 3 replace 2R pavers EX 3 repair bottom basement door hinge BS security 3 repair water main street valve EX $$$$ water damage 3.5 clean out chimney BS maintenance 4 1" PEX for basement water supply BS maintenance 4 properly cover sewer in auxiliary basement AUX health I haven't completely filled out all the columns, but you get the idea.Just know if you weather this storm, the seas will calm and give you time to improve your situation and prepare for the next wave. 

So the poor roof work would not be covered, but the resultant insulation and drywall work would be covered. what may be covered is turning in a 1st party property claim.

Roofing, foundation, major sheetrock replacement, insulation, and general remodel need a permit.Most handymen type of people are NOT licensed with the city as contractors.

I personally feel that it is worth it to further insulate me from liability.

I am selling one electrically heated unit this summer, and in another I have increased the insulation and put programmable baseboard thermostats in an effort to mitigate bills for tenants.

Read up on boat and RV storage a 20-25 x 45 or 50 brings a premium rent (no heat, insulated ceiling only) I believe these are classified S-1 (unheated storage).