Prepare financially by saving for down payments, improving your credit score, and setting aside emergency reserves.

You can also trade up these properties quicker into other properties where you can force equity.

A) The $40K cash on hand was not including my emergency fund and merely represented what I wanted to stick to as a low ~10% DP or to be used for a small refresh/reno. 

My piece of advice would be to research emerging neighborhoods and focus on areas with strong job growth and infrastructure development. 

For these reasons, we don't invest our emergency funds in anything that has volatility and we can't write a check against it the same day for an emergency.

My dilemma has been that I've gotten a little behind on some revolving debt that selling this property now could eliminate in addition to giving me cash on hand to trade into some better value or start a new construction duplex project I've been wanting to start.

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

I am sorry that the storm that passed through just prior to your stay required emergency roof repairs. 

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.

That said, you also want to be calculated on trading up.