With the right PM (I always recommend connecting with multiple who specialize in the types of properties you're buying), they should be able to help you stabilize the property and hopefully keep the tenants for multiple years. 

The tenant hasn’t been the greatest: late payment with not always paying late fees, multiple complaints from the neighbors, changing phone numbers, ect .

@Bob Asad I like the individual sub account method escrow account, but there are multiple different ways to hold security deposits and multiple laws in different states.

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

Yes, the more units you go up, generally the less players in the game so there is some advantage in purchase competition as you go up, but also more management scale and cap ex for someone who is new.3.

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

Local investor focused realtors will have multiple referrals for you to check out and interview.

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.

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).

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