Do you have contractors to get the job done? 

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'm sure there are plenty of paid mentors and coaches out there, but from personal experience its been the on the job 1 on 1 time with someone doing what you are trying to thats been most impactful to me.  

I've heard of mentees who started cleaning up construction areas on a flip at the end of each work day or picking up supplies at Home Depot and delivering them to the job site.

Give them money or they lien the house and walk off the job. 

Owensboro, the state's 4th largest city, has a population under 100K, and many OOS investors prefer cities with at least 300K residents and strong job growth.

STR's are a job. 

They did a good job and helped answer any questions I had about the 1031 exchange I did here in Chicago. 

In theory, you should be able to manage the job remotely, but there is a reason why I show up at least every other day.What is in dispute?

The lender will need to be able to prove on paper that you can afford all those mortgages with your job income and the rental income that you have.