How well can you manage multiple roommates?

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

For perspective, the rent is $2,500 and the pet deposit is $500.

Curious to hear the good, the bad and the ugly from multiple perspectives. 

I'm honestly trying to understand your perspective and I'm wondering if you're misunderstanding what we're all saying.

I appreciate this alternative perspective @Zeona McIntyre!

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).

You can read a book and multiple books, but unless you are out there doing it (I.e. getting bids and getting contractors to truly get you an exact estimate) you will be far off from the numbers you want and may even lose money on the flip/rehab.The best advice I would suggest in my experience is that you should get into the line of work by either partnering with someone or working with someone on some projects prior to going into a flip on your own.

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