Traditional limited approach or creative almost unlimited approach.

So if an Investor buys a property fair & square and then is approached by an end-user/another investor who really wants to flip or own that property.

I think a better approach is to provide a great rental at a good value so people pay and stay.

Therefore the deeper pocket buyers can buy the best products and the buyers that have to buy on the b-r-r approach with little to no money will get stuck if and only if they can't stomach coming out of pocket on a bad tenant run like you said.

After having some difficulty finding qualified tenants who could afford the rent, a highly qualified tenant approached me asking to lease one of the houses using an STR arbitrage model. 

We understand this can be challenging for our tenants, but we are planning for our children's future and teaching them about the REAL ESTATE benefits.Do any of you have suggestions as to how we can best approach this or can refer me to someone who can prepare a letter addressing our plans for the build?  

This approach can be a powerful tool in your real estate investing toolkit, offering opportunities to maximize returns while creating mutually beneficial deals for both you and the seller.Some books I recommend are:"Investing in Real Estate with Lease Options and Subject-to Deals" by Wendy Patton"Seller Financing and Real Estate Notes in the Dodd-Frank Era" by Dawn Rickabaugh"The Book on Investing in Real Estate with No (and Low) Money Down" by Brandon Turner and David Greene

Approach some people you would love to add to your team and make them a better deal then they have now! 

I don't know him or his system at all but I've seen enough of these to know that there's a 99.9% chance he's selling you a line of crap.

But your by-the-book approach and over-thinking are just not conducive to basic RE investing.