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..

@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. 

It's objectively rated as a great place to live, but obviously you need to be ok with Winter.

The STR was never fully utilized and their is some room to raise slip rates and increase winter storage.

Things slow down in the fall and winter and you might have less competition.

This also begs the question "Does it make sense to list a property for Fall/Winter move in, or are there more ideal times"?

You should look into setting up a cap for electric if you have hot summers or cold winters. 

you’re probably going to need it or people are going to move out when winter hits. 

And if winter move outs are a pain for you, I'm sure they won't want to move in the winter either.