I really like having multiple opportunities to make income from 1 property, including a worst scenario of converting all the units to LTR. 

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I guess it’s just a waiting game from here on out.

House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

So I require skin in the game (average is 5% to 15%) to offset this.

I recommend talking with an experienced broker who can help you shop multiple lenders  

Dont waste your time game-planning.

What tools or strategies are you using to stay ahead of the game?

I felt like checking a little bit more so I ran a proper background check on her and was shocked to find that she has multiple felonies including jail time.

Spending too much time on analyzing one deal will put you out of the game on too many other ones...