The first winter with the units in 2 buildings went fairly well.

You can be any luckier then to get to spend your winters on the beach.  

Hoping its just winter and things will finish soon.

Rural lands especially pre google earth etc was and is a specialty it was a waste of time to list them Other agents could not even find most of these parcels 10 to 40 miles back in the national forests on dirt roads etc etc..

Quote from @Marc Winter: There are water leak detection alarms you can install in the basement--probably some that will alert on your phone. 

The move-out timing could suck if it's over the winter, but that could happen with any tenant at any time honestly. 

Might be similar profit to airbnb in the winter in chicago but I don't know firsthand. 

@Sebastiano Cantali Millvale, Etna, Sharpsburg, Brighton Heights, Carnegie, Swissvale, Homestead, Munhall, Carrick, Observatory Hill, Forest Hills, Bridgeville, Brookline, Beechview, Overbrook, Coraopolis, Ambridge, Crafton Heights are some that come to mind.Key is to focus on areas that aren't too high end but also not too rough.

.: 21-24 month lease, so it ends in spring, not winter:“Assuming ZERO late payments or lease violations the rent will be reduced $100 (or 5%, whichever is lower.) for the last 6 months of the lease.”That’s a 1% discount for a “good tenant” I assume you would accept 1% less for zero late payments and violations. 

Everyone in this Industry at least who sells RE to Homeowners NOT investors knows the cycles and right now the cycle is MORE LISTINGS period nationwide.. then come about Nov.. people slow way down B/C of the holidays and in other markets winter is slow because weather is so snotty..