Or subs or property managers who run off the rails. 

Without accounting for management fees (I have not yet decided if I will try to self manage), and with planning to raise rents to typical market of $825 for each of the smaller units, and $1200 for the larger unit, does this seem like a worthy first investment? 

I have several really good lawyers we use, you can PM me if you want info on them ... and if you'd like to talk property management reach out.

It's an estimated cash on cash return given current rental rates subtract expenses assuming 7% interest rate, 10% management fee, 5% repairs, 5% capex and other expenses like mortgage, insurance, tax. it's a estimate to tell you what properties to analyze vs ignoreyou can see the are pockets of negative returns as well as pockets of positive return. this is to supplement the data @Devin Conley provided

And you can do it with little cash, 5% down conventional is better than 3.5% FHA.House hacking also gives you a chance to cut your teeth in all major skills: analyzing deals, buying process, financing, working with contractors, advertising for rent, background checks, property management.

Your account structure depends on your goals for growth and if you plan to self-manage or hire a PM.

If this is your only rental, it's more about if you want to keep the property from a management perspective.

➡️Manage existing portfolios.

If you move, renting in NYC and buying an out-of-state property could work, but make sure you have a solid plan for managing it.If you stay, buying in an affordable market and living there for a while could be a good option.

And if you are need of MTR management services, my company, Island Stays Hawaii, provides premier STR and MTR management services.