So they price those homes at what a willing homeowner will pay for their personal residence.

This way if there’s physical damage by residents the company pays the first $500 to fix it.

But you'll have to either manage it yourself and develop a really good skill set in that or get a smaller company that doesn't have too many properties to manage who has a high skill set management for you, but then you need to pay for that.

Now if I pass that income as management fees to S-corp, I pay $3.5K (SE tax) + $800 (LLC fee) + $1700 (CPA + bookkeeping) = $6K in total.

If your situation hasn't changed much, it might not be worth paying more for premier.

Our tenants pay $2,700 in rent and the mortgage+fees comes out to $2,360.

If you want good contractors out there quickly , pay their price and pay it quickly . 12 months is too long , we can build a 3000 sq ft house ground up in 3 months . 

My profile has my YouTube channel and I have an episode that shows you exactly how to create the comp set and look at amenities that matter, what others are paying for cleaning and how other listings look - that way you can see how to best market your property. 

If your willing to do so, you can live in the casita and then rent out the main home and have your tenant pay the majority/all of the mortgage (depending on what type of deal you find obviously). 

Is it worth to pay that much for 1:1 coaching for 6 months and a laid-out course?