My 2 cents: You're young, you could get a real estate or real estate adjacent 9-5 so you can get paid to to learn more about real estate while learning and building the side hustle outside of business hours.Seems like you live in a major US market so that's a plus, you could get a tenant services coordinator job in commercial real estate making $40-60k (not sure if that's more or less than what you are making now) It's an Entry level role, anyone with a degree and a polished resume and a passion for real estate should have a decent shot at landing a job like this.

We had a wash & fold service with pickup & delivery, which added complexity to the operation.

I don't necessarily need the standard features of pm software, such as rent collection, bookkeeping and maintenance requests, though that could help; but do need a clearinghouse of important information, such as leases, legal docs and other information; maintenance vendors I use; maintenance history; and some kind of tracking system, where I can record the various current projects I'm working on within the business.

This extra road frontage now also qualifies my property to be able to be legally converted into a triplex from a duplex.

@Alecia Loveless is correct--tenants need access 24/7 to their electric service panel, water and heat, assuming those are individual utilities for each unit. 

Make sure it explicitly explains the process for termination if you are unhappy with their services, especially if they violate the terms of your agreement.3.

This area definitely gives you good weather year round, summertime gets hot so as long as you're getting systems serviced before then and then in the fall you're usually ok. 

Because Airbnb only makes money when the guest books on Airbnb.Hence, they want the price to be cheapest on their platform, so people book on Airbnb instead of elsewhere, and want their properties to be able to compete with hotel prices (even after cleaning fee and service fees). 

We specialize in short-term rental investments through our integrated real estate, mortgage, and property management services, delivering expertise at every stage of the process.

Have you talked to any social service agencies about this yet?