This reduces the number of deals available substantially.I would not attempt a sub2 without an attorney doing the legal work.

How do you normally handle insurance?

I also handled all the paperwork including tax, insurance, etc.The condo was in fair shape, but many of its components were dated.

How would you handle needing to replace a hot water tank, leaky roof, landscaping or something else?

Interview them about how they handle maintenance, late rent, unpaid rent, lease violations, evictions, etc.5.

Will the title company handle the paper work for the land contract for us after I send them the purchase agreement, and if so, about how much should it cost? 

If I knew an attorney, or know how to resolve this situation I could handle it, or just sell the deal, as there is good profit there. 

While AirBNB is certainly imperfect about how they handle resolutions, I think there are some valuable insights here about the necessity of documentation.Putting myself in AirBNB's shoes, photos and invoices are absolutely critical to resolving disputes and damage/expense claims - otherwise, they would be at the mercy of people who wanted to abuse the system and make frivolous or false claims.  

So any way you can improve operations (raising rents, reducing vacancies and expenses) will have a compounding effect on how your business is valued (code for forcing equity), allowing you to potentially refinance and get cash out of the property to use toward future acquisitions.Tenant experience. 

If your goal is to reduce that self-employment tax to a minimum, an S Corporation is the best entity to use.