After several phone calls and meetings, with accountant, financial adviser, and attorney,  (my team) I have decided to go with setting up a new LLC for this property.

I'm definitely looking at ARV in setting the final rent.

In our area, the town does provide recycling cans - usually we go and get them from the town when we first set up an apartment - if the tenant breaks or loses the can, they are responsible to go get  a replacement.The town does provide garbage service and the tenants can put out up to 3 garbage bags at the curb on pick-up day. 

That is only $40 per month set aside for vacancy costs; it would take 10 months to have enough set aside in a "vacancy reserve" to cover the costs of just the mortgage payment for ONE month.

If you can find the right deal, you'll be able to set yourself up for success.

PMI is a set rate, you can look it up, I believe 1.75% upfront which gets added in your loan balance, plus I think .85%/yr added to your monthly payments.

It is always important that you set firm screening standards and never waver.

The issue is that this single property has a need for a specific skill set, my father in this particular scenario, and this same job will be outsourced in the future.

I'm thinking about a few options:  1) Airbnb it, 2) rent it out, 3) sell my house (with this new unit) or 4) convert both structures to condominiums (if even possible).I'm also considering renting out my own house too (single-fam), ~1,500-sf, 3BR, 3BA. 

If you would like to get set up on hotsheets to watch the area I would happy to help.