Crying ….as you say not relevantHealth issue.... not relevantMarket rent...extremely relevantCost of tenant turnover....not relevant (cost built into expenses)The cost to you of reducing her rent is:late payments, chasing her for rent, excuse after excuse, ultimate eviction and vacancy plus a loss of $100/ month in the interim (plus a guaranteed lose of a minimum 1 months rent, if not more, before you ultimately get rid of her.)  

I gotta be honest I'm not entirely sure what that means but I've plugged that into my monthly taxes anyway.

Assume you'll hear that the house is worth it when it isn't, tenants are good, management will handle everything, it will be easy for you, vacancy and non-payment will not be much of an issue, repairs won't cost that much.Some will be honest, some won't. 

Meeting someone face to face, seeing the market, touring some props, and getting a first-hand idea of the operation is extremely helpful.

This is a very subjective question, and honestly depends on what you're comfortable with, and also will depend on the market. 

Honestly, HVAC stuff is an area I need to learn more about, so I have shyed away from this property.

Is this a one time venture or does this partner have extremely deep pockets to keep funding your deals?

I’d definitely recommend employing a value add strategy regardless of which path you take.I’m house hacking a 4plex in an A+ city in the East Bay, but those types deals are extremely rare and you have to be well connected to the brokerage community to have any shot at getting them.

For the sake of your future CPA, do not wait until tax season ;)At that point, we're extremely busy and the timing may actually prohibit us from taking on new clients.

I feel like there's a lot of enthusiasm for rental properties, but to be honest, it all seems really overwhelming and I never actually feel comfortable starting.