I’m looking for actionable steps with hard numbers to find that deal, make that first decision. 

Before making any decision, I would get a customized property evaluation by a local Realtor to determine the value of the property on both sides of the spectrum; sale OR rental. 

So PLEASE don’t make another huge financial decision and then tell that same person after you do it.

Good luck in your search and decision, I'm sure it will be a good one!

I will give this some more thought before making a decision.

@Anthony KolbuszBRRRR method is a fantastic strategy, especially with your trade experience.

Most importantly, how can I set realistic, effective metrics to guide my investment decisions?

As for your Index funds, if you were trading indices such as SPX, you would have the favorable tax treatment accorded to §1256 Contacts:  60% of gains are Long Term Capital Gains, and 40% are Short Term capital gains.

The model won't be perfect, but should be a very helpful decision maker for when you can safely leave your W2 and establish your budget going forward.

However, after dealing with the constant headaches of repairs, complaints, and other issues, I made the decision to shift my focus to larger commercial deals in partnership with others.I have co-founded a coinvesting club, allowing me to diversify my investments across multiple deals.