Sometimes it's nice to get a new lease so that you can increase the rent right off the bat, but having tenants with a solid payment history is worth so much more to me.

Much cheaper to keep it nice and cool.

Your story sounds like what you hear when someone has gotten divorced, or lost a high paying job and had to sell or lost the home to foreclosure, along those lines. 

What I fear about that set is what happens when Josh wants to get a new job? 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

It's nice to see the community showing support for STRs and pointing out that an STR doesn't solve any of the real problems.  

Great job for taking the leap.

It was nice to see you actually tried to answer the question.

Provide copies to all parties involved.This project-specific agreement works well for one-time jobs, but if you plan to work with subcontractors regularly, I highly recommend having an attorney draft a Master Services Agreement (MSA) for your business.

A friend of mine in Austin once negotiated a partial buy back option when the seller realized they might want back in if the market soared.. from what I read in Bloomberg, that approach can work well if both sides trust each other.If the tenants’ rent covers your carrying costs, that’s a nice cushion, but you still need to clarify that buy back clause.