But after a exhaustive search, I concluded platforms like Cozy.co and Avail.co are just not good for rental management. 

If that LTV's still too low, I'd give up on the HELOC option.If I were you, I would first try exhausting balance transfer options for Unsecured revolving at 0% APR, and if that fizzles out, Sofi or equivalent could lower that rate drastically on an unsecured consolidation.

I'm in the camp that says you should exhaust all of  your conventional loan options before you get a commercial loan that will cost more with a lower loan to value. 

You are roughly looking at $330/square for architectural shingles including tear off and haul away, drip edge, plumbing and exhaust vents and ventilation system. 

I think if things get to the eviction stage, all other options have been exhausted, so you must do what's necessary. 

If the numbers you provided are accurate then you should exhaust every possible option (like it sounds you are doing) before giving up on this deal.

For example, if it is a couple middle aged guys then you could let them sweat a bit, but if it is a little old lady that is sensitive to heat exhaustion, I might replace it sooner than later. 

Let's say you take your vehicle to the mechanic and he tells you that you got a bad exhaust leak, you don't just go out and buy a whole new car, you get it repaired.

Having a parent in ICU, on life support, or comfort care/ hospice is emotionally exhausting, so I am guessing son may not be at his best. .

Avoid high risk properties (some C and all D class) until you are experienced.This is not an exhaustive list but will get your startedGood luck.