There is no grade on their roof to guide water to my drain/gutter...just a break in the flashing that divides the two roofs.

I didn't see how much you payed initially for your condo, so can't really say how much your PITI is, but my advice would be to re finance out so that you essentially break even monthly, then take that & invest in a section 8 multi family to balance out your portfolio.

Don't incentivize a longer lease, it doesn't buy you anything, people break leases all the time

We are afraid they might tell us to break it down or something.

i dont want to break the bank would this way be more expensive then just hiring out a GC?  

Even buying 2% multis at a 14 cap back in 2003, my break even ratio was 6/9 or 9/12 with debt.

Every month I stash a little more away to protect my self, the asset, and the tenants living there should something break.

I have done a rental credit with a different tenant in the past for a different issue, they ended up breaking their lease anyway and it was really money down the drain in that instance.  

Maybe if the land was given to you, and the insurance and taxes were very low, and it was right on a body of water?

If the situation is that bad i.e. causing health issues then give the tenant an opportunity to break the lease and move.