Starting out...

[Kobus Ryan]

Hello everyone, 

I am just getting started after years of being a "wantrepeneur." My current situation is this, I purchased my own house a couple years back that is my girlfriend and I primary residence. We have a condo that is being rented out and paying for itself (and gaining about 100 bucks a month that goes into an account that we don't touch.) Like everyone else here I have the dream to become financially free and work because I want to, not because I have to. We are looking to get into rentals and I feel that being a buy and hold type of investor would suit me the best. 

My question for those more experienced than myself is, should we hold onto this property and see if that property appreciates? Or, should we sell that property and take what money we would make off of that and pay off our debt and reinvest what is left into another property closer to home? The current rental is about 2 hours from our house. Money is tight right now so we do not have 20% for a downpayment on something new. 

Any advice/input is greatly appreciated!