Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

and they charge per door and not sure if they even offer everything that I want. 

I think our best client in the last 4 years we probably made them $750,000.Then I get the call from the one property owner trying to nickel and dime me that we will charge $190 for his townhome and he can get someone else to do it for $125.

BUT The points they charge and interest are both way higher than normal, on some deals I ran numbers the points and interest were going to be 20k on properties where the ARV is 100k so you have to get properties at such a low price to make it work that it is so hard.

The meters are rented and the monthly fee ($7.50) can be charged to the tenant on their statement. 

Explore the possibility of doing liability insurance instead, if you don't have much equity it may be your best, and much cheaper option.  

My lease has a sublet fee (2 weeks is guest by lease more than 2 weeks in a year is sublet) that is costly enough ($100/night per person which is about what a cheaper hotel is here) that makes sure tenants do not have others move-in without informing us.

So, if you buy an older home it's typically much cheaper, since you're not paying much for the structure. 

Quote from @Aaron Wolman: Yes, these charges are fair.

What if, upon an imminent snowstorm, Home Depot began charging $200 for a snow shovel, just because they could?