Just speaking to the first point, you can definitely hire a property management company to handle your airbnb.

If I wind up in a pinch then I’ll dip into my personal cash reserves.  

@Chi SastryYou need to define "good market" Franklin TN for example is the best market in the entire world if you want to live there personally.

Also, how would you handle a similar situation?

Personally, I assign my deals to my end buyers when working with sellers to help them find buyers for their mobile homes. 

My question is how long do you personally wait to see how your Airbnb venture is going to go until strongly contemplating long term?

To what extent you tell them how you structured the deal, bought the property or anything personal for that matter is up to you.  

I suggest you look for the title companies who handle the loans for local hard money lenders.

Come to find out his wife's dad had a career in real estate, his friend works at a firm as a private lender (that's how he got started), the houses were 50k houses and half of them were trailers...His personal house, while large was in the middle of nowhere...You can see the focus shifted from real estate investing to social media marketing.

The reason I changed my mind about John Jackson is, after years of being investor friends, he asked me to be his acquisition person, help train his students and to speak at his seminars.