Almost every time, brokers will ask what kind of properties you look for.

@Karolina Powell what we've experienced in handling both is the struggle for tenant stability.Logically, the more people you add to any given situation, the more likely it is that at least two of them won't get along:(We've placed a new tenant in a duplex several times and had them not get along with the existing tenant. - Sometimes we lose both tenants, but often we can keep the longer-term tenant calm until we get rid of the newer tenant.This is more difficult to do when you place a new tenant into a 10-unit building where all the other tenants have been there awhile. 

I feel as I'm expanding that having an accounting software to track/categorize my expenses would save me time.

I've had rentals for awhile now, but this is the first time something like this has come up. 

Maybe you get it done easy enough some times, but then other guests won't sign it because ... they're lazy, they're unsure why you're doing something separate from Airbnb, for any number of reasons. 

We have a disabled son and can’t maintain full-time residence there so that’s why we’re selling.

Do that a couple times.

If you do not, I would still love to connect sometime when time permits.

I obviously want to pay the lowest taxes over time.

Full disclosure - I broker these types of loans.