If they are changing jobs, they need the new job first and you need to paychecks or offer letter with salary or maybe even the first two paychecks at the new job, depending on their level and income.Ask them about deposit and rent. 

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.

I really appreciate you taking the time and digging in together so I was able to get a full picture of your expectations and how we can do a better job for you and other investors.  

Lawyer’s wet dream. 

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

By a professional estimate I mean having a contractor bid the work, not just me estimating the jobs. 

I am not sure what type of real estate investing you're considering, but it sounds like, with your family and busy job, you won't have a lot of time to be hands-on or personally involved. 

Markets, geoglobal conflicts, recession, inflation, jobs can all affect that but time will tell. 

But if your goal is to leave your day job soon, multi family will offer more cash flow typically.

In my day job I’m an ops professional who manages a tech stack and efficiency is important.