I can have someone periodically clean them up.. would that be more cost-effective than spending it on gutters?

With little to no experience in pricing out reno I run a low end estimate of 10k to refinish hard woods, lay floor in bath and kitchen, hang drywall in all 3bed and 1 bath, and paint everything.

KNOW what you get for different price points as far as quality of construction, cabinets, faucets, flooring, appliances, etc.

After they moved out, I was doing the tenant turn over (cleaning, painting, etc) and one day while I'm there it starts to rain. 

"We strive to provide safe, clean, affordable, comfortable, and quiet housing for responsible renters."

Are they keeping the place clean - no holes in the walls, etc?

I estimate some electrical work, kitchen rehab, painting, & flooring.

Last night we had a contractor come in, assess the damage and then work on cleaning it all up, drying it out and spraying.

I discovered that there are flooring issues in one of the bedrooms so the contractor will need to cut the floor up to see what’s going on.

It's hard to find deals right now, but if you're the bank (cash purchase) or you don't care if your returns top 7 or 8% (institutional buyers) then you're going to clean up nicely because competition has greatly slowed.