The exterior appears to be in decent shape other than some landscaping that needs sprucing. 

Maybe install an electronic lock to get them access.

Invoicing electronically throughout the whole bill, receive payment, deposit and reconcile cycle can ease the bookkeeping burden.

The bad: Needs updated baths, kitchens, refinished floors, paint, deck and landscaping at a minimum, basement is gross. 

You might get a break if you don't need the stump ground down (and can landscape around it or something.Then I would actually look at (again back to bids) getting a new concrete driveway.

Electronic darts are an alternative to the pool table, $30.Be prepared for things to break on a Sunday, and you'll need to fix it pronto. 

Is there any legal issue I would run into if I only kept scanned copies of leases electronically, or better yet, only had completely electronically generated and signed documents like real estate agents use?  

I actually had a listing in Laguna Beach that was a completed flip with everything done inside and out, down to the studs, with exterior painting and landscaping, listed in the high $800K's. 

Now, I've tried electronic rent payment service where they automatically deduct rent from the tenant account on the first.

So tomorrow I'm headed to the property to look at the boiler to see if the water was high enough to damage the electronics or any other parts of the unit, and I'm planning to have a local heating company come out to inspect the unit.So this deal has already been crazy and stressful, but that's real estate.