Seems like the best way to keep most of my money.

I WILL keep this short.I am 23 years old, me and my Dad have been investing together over the past 4 years in real-estate....we just closed on our first deal which was:275k Home which we bought for 255k......That home is nice but does not cash flow and just pays the mortgage. 

Its a 2 family home in a rough neighborhood, one side vacant and the other is occupied.I have an okay relationship with the existing tenant but it has been a constant struggle with late rent, her keeping the property a mess, and her unit is disgusting, etc. 

Can I keep the deposit if they bail?  

You keep your current loan AND free up your equity to invest. 

I currently have a 5 bed 3 bath home, that I plan to keep, and turn into a rental, as it will easily rent for more than my current mortgage.

. -- You'll keep back maybe 5% of all rents for routine maintenance and another 5% for capX (big expenses like roof or furnace replacement).  

I'd be patient, keep looking, inspecting, and making offers that work for you.  

To see how you are with being a landlord again, then gradually scale from there. with the remaining cash on hand, you always have the option to pay it off whenever you'd like or keep it on hand for any repairs/ maintenance that comes with being a landlord.  

Keep in mind you are responsible for the utilities, internet, upkeep of furniture, bed sheets, etc.