I'm considering numerous options here..

A portion of roof needs replacement and their are numerous repairs ranging from basic to intermediate throughout the property. 

BP has numerous articles explaining how to screen tenants and if you follow all the steps and don't cut corners it is not difficult to find reliable and trustworthy people to rent from you.

There are numerous estate sale companies who will help you out with this for a percentage of the profit, or if you have some time you can list it on Facebook Marketplace or Craigslist or similar.

I’m resourceful, I sell homes that I renovate and have a variety of contacts who can help with mortgages

Sometimes it's ambiguous, but even then, why should I bother with the company that has numerous unresolved lawsuits, versus another company that is virtually the same but has none.

I have watched numerous podcasts, numerous YouTube videos trying to educate myself on what to look for.

These have 30 year mortgages and a variety of benefits and drawbacks, as each lender is different.

Coming into the closing scheduled for next week on a single family home and the lender hit us with some repairs required prior to closing, or place money in escrow yesterday based on professional licensed contractor quotes (a sample list below of the numerous items they requested).

@A Schwartz While you already received numerical feedback to your question, your best bet is to reach out to mortgage brokers and speak with them to get a fully detailed answer.