For the multi-family, we go by every 2 or 3 weeks to do lawns in the summer, and depending on the snow load, we go by every month or less in the winter to plow. 

I use a standard renters agreement that I have modified (for snow shoveling) and so far it has worked.

And make sure to account for the following expenses:1) Mortgage 2) Mortgage insurance (PMI or MIP) or FHA Risk base3) Property Taxes 4) City Taxes5) HOA (Home Owner’s Association) Dues and Fees and Assessments 6) Insurance  a) Property Hazard Insurance  b) Flood Insurance   c) Earthquake Insurance   d) Umbrella Insurance7) Vacancy Rate (usually 8% - the equivalent to one month a year, or 5-6% if multifamily and/or if experienced, if not use 8%)8) Utilities (you’ll have these if your tenant is not covering them and/or during vacancy)  a) Water § Sewer § Garbage  b) Electricity c) Natural Gas d) Propane9) General Maintenance (usually 5%)  a) Upkeep § Landscaping  b) Snow removal  c) Repairs   d) New Appliances 10) Capital Expenditures (usually 5%, higher is the property is old and obsolete, less if fully rehabbed and all mechanicals and roof are new)11) Property Management (8%, even if you self manage, your time still has value and there might be a time when you'll want to be completely hands off or you'll not be able to do it, vacation, retirement, etc.) 

I plan 100 for trash, snow and water.

There was fierce competition on the property, which is justified because the most conservative NOI is around $2850 giving it a CAP rate of 8.5% and a nice COC return around 10% - 16% depending on how expensive lawn/snow/water/common area utilities are for the year. 

No desire to go back to snow.

(2) Does anyone have any recommendations for a snow removal service?

there's also no lease. they're month to month and i dont have to do any rehab to get it to 500 a month. he was a friend of the owner and took care of lawn and the snow removal which is why he was at 275

I also don't see lawn care / snow removal.

Also, this house sat for 17 months so once the snow melted I realized how bad of condition the yard was in.