If they get well each month and aren't bad tenants in any other way, keep collecting the late fees making the extra income. 

I'm looking for a few options to do a competitive bidding process on the repair (I'm not sure how extensive the repair would be).Thanks in advance for any suggestions.David

One of my main goals is to have units and tenants that my wife can manage and safely collect rent or do the inspections on.

The C Corp collects a management fee monthly from my rentals, and it's charged off on the schedule E.I also have a active business thru an LLC with employees.

So if it were me, what I would do is when you collect the keys just ask them for a forwarding address where to mail any balance of their security deposit that may be due to them. 

And, btw, my agent pretty much said I'd be on my own for this type of deal since she couldn't collect a direct commission from the sale and didn't feel comfortable with it to begin with. 

The GP will be doing all the work and I'd be just sitting back collecting checks.

The architectural style of the house makes it challenging to put gutters around the front roofline  due to some overhangs ( 2 on each side of the house that goes straight out in a rectangular shape like an inverted U shape but with sharp straight corners and there’s 1 middle overhang that’s like an inverted V shape that is also attached to the roofline and come straight out of the front so  rain water will come from those as the overhang covers a portion of the front and will kind of serve as an extension of the roofline. 

I made the same argument at first as well for someone with multiple rentals (As I do for like...home office deduction, if you're managing 5 rentals, collecting rents, screening tenants ect...I am comfortable taking that deduction- I was going to apply same here but saw a no aggregation wording) 

Needless to say, roofings usually last more than the estimate time, thus, if you think that it might last 2 years, it end up lasting 5 years, in the meantime you can collect rents to pay off the roofing and maximize your cash flow.