The light in the unit was awful, I had a blood-red fake leather couch, and I took horrible photos with my cell phone.

It's the middle of the winter in Chicago.

yeah the tenant pushing back is my concern. it just so happened that this happened with the tenant that seems to not like paying. and the heating is electric and this winter has been extremely cold which caused the electric bill to jump up to $800!

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing. 

Got a negative review for not having a garage to use in the winter….

Quote from @Pat Aboukhaled: Curious.. do you think a flat rate for the whole season feels more convenient, or would you rather pay per snowfall to avoid paying for a mild winter?

Quote from @Hunter Hanlon Taylor: Hey, all, is anyone familiar with any good contractors near the Columbus, Ohio area who would be good for various updates I need done on my STR this winter? 

We manage between 80 and 100 listings it varies winter to summer but the processing of manually Remitting and paying out the property taxes takes much longer than 10 min.

Looking to purchase a duplex, triplex or fourplex in Panama City and do short term rentals for summer months and long term through the winter. 

I own all my toys, never seriously worry about money (I suspect everyone with any money always at least pays attention to it), spend my winters in Florida and rarely work in any sense (I do some consulting and side teaching) more than 10 hours a week.