The unit has a sort of basement apartment, but it’s all one unit and can’t be rented as a second unit, but the whole house has legal occupancy limit of 8.

You must be an owner occupant, but can get draws for rehab costs etc etc with potentially as little as 3.5% down. 

But if it is not you are limited to 180 days/ yr occupancy and need special license.

For some reason, a lot of northern towns are FREAKING OUT about having too many STRs & they’re adding a lot of regulations.Another reason I invest down south is bc of the higher year-round occupancy.

It grossed ~$73K in 2019 with only 40% occupancy (cash flowed about $20K). 

Your occupation (contracting and restaurant work) are seasonal and in unstable industries.

An owner-occupant requirement like that seems a bit strange to me coming from the zoning department - if you were talking about some other entity government entity like HUD, it would be less surprising.For your reference, I own an investment property (SFR) with an accessory unit in the City of Aurora and have never heard of such a requirement & I don't live at the property.

If you buy a property at 100% occupancy, a lender will still use a vacancy factor based on local rates.  

We paid all cash and bought the complex for $1.2 million.Two years later, after roughly $400k in repairs and operational expenses, and bringing the property to full occupancy, we refinanced the property and pulled about $1.8 million out.Today the apartments are still fully occupied, rents have gone up and it is currently valued at between $5-6 million. 

I've been researching various strategies for how I would like to invest, and there are some interesting hurdles that I'm enjoying thinking through given my occupation and physical locations.