The first time I rented out to a handyman, I made the huge mistake of giving him a discounted rent for standard maintenance on the property(changing filters/mowing/snow removal). 

But it’s hard for a “rule” to account for Texas property taxes, snow removal in Buffalo, owner-paid utilities vs. 100% separate metering, etc.Additionally, it falls down at low or high rent levels.

About the only thing I know they cover (he told me some of the stuff on the phone) was replacing roofs and cutting grass and removing snow.  

What are the strategies I can use to speed up this snow balling effect? 

Here's what I put in:Income (given in the property description): $1895Expenses:Taxes: $245Insurance: $55Lawn/Snow: $50Vacancy $100Repairs: $200CapEx: $100Mortgage: $750Total: $1500That gives a cash flow of $395/month or $4740 annually.Cash on Cash ROI:Down Payment: $4800 (given what I have now in the bank I could use to invest)Closing Costs: $3000 (just went with what BP had in the video)Rehab budget: $1000 (it looks like there's tenants already living in part of it it so I'm wondering how much could even be done right away, if much at all)Total: $8,800Divide it out and you get the ROI I stated above.

Upper main roof first half replaced 8 years ago, second half replaced last year, and lower roof was replaced last month.4 Separate Crown Aruba Gas Boilers, regularly serviced and approximately 20 years old. 4 Separate Gas hot water heater (ages vary)Washer Dryer hookups available in basement for coin laundry for additional incomeExterior painted two years agoShingle sidingProperty just passed state inspectionReplacement energy efficient windowsPurchase Price: $210kAppraised Value: $285kProperty Type: Quadplex/Turnkey tenants in placeArea: BUnits: 1-3BR, 3-1BRRental Income: $3365 Per Month / $40,380 per year (rents can be raised 5% upon lease renewals)Utilities: Separately metered, each tenant pays their own gas and electricHouse Utilities: Common area utilities are about $20.00 per monthWater/Sewer: Landlord pays $1500 per yearProperty Taxes: $7855 per yearInsurance: $2500 per yearLandscaping/Snow removal: $1221.00Vacancy: ???

Tripping hazards, snow, dogs, etc. can wreak havoc on that situation. 

Same thing with snow plowing.

On the maintenance side, don't forget lawn care and snow removal in the winter.

This water thing has happened twice now in a month or so, despite heavy rains and melting snow.