I have STRs in Buffalo/Niagara but that's far upstate and not something I could do for a weekend trip =)

I found this deal by "stumbling" on it during a weekend get-away trip with friends for a celebration on another property.

We are taking a trip down in July to check on things.

The majority of existing houses were built in the 1930s, contributing to the unique character of the neighborhood.

Cracks in driveway are fine unless like multiple inch difference in heights (tripping hazard) and the window would need to be fixed.

For example:General-Filters (furnace, air conditioning, oven exhaust, refrigerator, and water)-Stove burner when the “eye” needs simple replacement-Batteries and remotes that service the premises-Fan and light pull strings-Smoke and carbon alarms testing and batteries-Ensuring appliances are properly plugged in, hooked up, and used-Removing dirt, debris, and lint in and from connection pipes (e.g. clothes dryer)-Tighten loose screws on all home functions (e.g. doors, hinges, handles, socket -Balancing off-balance appliances-Cable, internet, and phone jacks-Fire extinguishers-Systems operation (e.g. security, irrigation, HVAC)HVAC-Monthly A/C filter and drain line maintenance Electrical-Reset “tripped” GFI breakers-Light bulbs (throughout and at the end of the tenancy)-Blown fuses-Reset breakers in the outside and inside breaker boxes-Socket and plug outlet coversPlumbing-Unclog drains or toilets-Caulking around tubs and showers as needed-Gas pilot lighting-Leaky faucets and shower heads-Toilet flappers, handles, seats and seat lids, tank lid, and flush kit-Sink and tub stoppers-If septic tank present, use RID-X as directed on consumer box-Proper cleaning of garbage disposal-Loose faucets and sprayer heads and hoses-Faucet filters (i.e. aerator)-Open exterior plumbing clean out when necessary (e.g. sewage backup)Exterior-Routine lawn (and pool) maintenance-Adjusting sprinkler heads as necessary-On the last month of tenancy, tenant must perform required lawn maintenance no sooner than 2 days prior to vacate dateThere’s a lot to consider as a landlord.

Having a good judge of character is important here too, but again not a guarantee. 

He is organizing a trip to Houston for free to train people.

Also since its a rental you definitely want umbrella coverage as if someone trips and falls, you would not be covered by insurance and could be on the hook

It was both, but knowing how they treat property is also a good indication of character despite a poor credit rating