Can I ask why you want to rent out a short term rental instead of buying or renting out a whole unit that you already own to a tenant on a one year lease?

Much less frequent, but we also weren't allowed to participate while my husband was a housing commissioner, as it would have been a conflict of interest.

I want to be somewhat hands on so I would pick markets that are driveable for you and visit frequently. 

It takes a lot of time for them to reply to my messages (which are not many) or send me a copy of the lease. 

If you actually have a triplex rather than a duplex that could impact insurance eligibility and pricing but it doesn't sound like that's the case.Along those lines, you just have to make sure sub-leasing is OK with your insurance.

More interested in land contracts and lease purchase options enough /without needing a lawyer each time.The properties are worth about 150k each.

The landlord or his agent shall notify the tenant within 30 days after the beginning of the lease term of the name and address of the bank or institution where his deposit is currently located or the name of the insurance company providing the bond

Besides we're hospitality people, not selling property or leasing it long term, and somewhere along the line a few states got their definitions very very mixed up!     

People are touring and signing leases the same day because of the urgency to live somewhere.

I've found a potential tenant that would love to do a lease option, or rent it with the option to buy at the end.