I did whatever it took to stay above water.

Tax's super low here No state income and cap ex super low.  10 to 15 year old houses this one had new condenser water heater Stucco house Tile roof Desert landscape.. bullit proof..

Eventually, when the cash flow from the rental properties is enough to replace my day job, I'd like to transition to managing my properties as my primary job.I'm trying to test the waters to see if this makes sense from a business/tax perspective. 

It has a great water view of a nice pond with a private dock.

How old is the roof, the water heater, hvac, appliances, flooring, siding, etc.? 

Might be NBD, but don't make that assumption.Is water and sewer are separately metered, the tenants should be paying that expense.What about lawn care and snow removal?

Kindly help me with your wisdom.It’s a semi-detached 2 unit has a new boiler, new hot water heater, vinyl replacement windows, brand new exterior doors, completely renovated 1st floor- 1 bedroom unit - features a living room with a fireplace and granite in the kitchen, ducted for central A/C.The 2nd floor-2 bedroom unit has central A/C.There is W/D hook up in the basement, and also a W/D hook up for the upstairs unit (would need stacked small unit to fit into space).

The plumbing is galvanized and hot water pressure in some units is maybe at best slightly more than a drip.

The home is on city sewer/water. 

Any other bill, companies will work with you, electricity, water, cable etc... but landlords largely remain inflexible.