The area has suffered from stagnant population & job growth and gets a lot of negative press due to the amount of snow(it is a lot).  

. $1009Taxes: $260Insurance: $208CapEx: $180-360Vacancy: $180-360Lawncare/Snow Removal: ?

(I.e. did it see alot of snow, rain, wind, etc.)

With regards to the driveway specifically, if snow is a factor, that should be considered.

Then as the landlord you might only pay insurance, garbage, HOA fees and lawn/snow.

I mean he will never have to worry about filling in a vacancy ever and I told him even if I don’t have the place Sublett at any given time he will get his rent like clockwork every month and what she does until this day. 5 other STR I have and I offered free snow removal in the winter time And (4)  free landscaping visits  composed of 2 in spring and 2 in summer which my brother (who owned a landscaping  company?)

We had 30" snow last weekend, and temperatures rose today to 45 degrees and pouring rain.

If you don’t have a contractor by the time you close the deal then you’re gonna be suffering holding costs from that hard money lender, taxes, lawn or snow maintenance etc you’re gonna need to find your house your financing and your contractor, you should have three or four contractors, all at the same time manIt’s not baseball it’s juggling Read Bigger Pocket “diary of a new Construction Project” J Scott  it’s step by step

Depending on the notice requirements of your state and city I would make sure to get my renewal notice ou the next day Reminding the tenant that starting February first they would be on a MTM lease at this new higher rent (Market plus hassle factor $’s) and that starting that date tenants would be responsible for all hvac upkeep (filters and duct cleaning) and all landscaping (snow removal, weed whacking, mowing, etc) or they will be charged a $100/mo maintenance fee. 

@Matt Snow short answer.