@Andrea Castor I've definitely decided to go the route of paying off the cards. I actually made a nice dent in one of them this morning....the other will be a work in progress and take a few months. I will definitely not look back on those!
As for the car, I've kept cars as well (probably some longer than I should have), but I also travel back and forth to NJ every other month in my car, my parents and majority of my family live there. I probably could've gotten away with something a few years older with decent mileage...but I plan to keep this one til the wheels fall off, lol.
My hope is to be able to be doing this full time within the next 2-3 years...so I would have to pursue it pretty seriously in order for that to happen. I would agree that I need to get a few deals under my belt first though before I dive in.
Yeah, he's supportive. Of course he doesn't want me to do anything that would put me in a position to not be able to cover my own bills...but he is on board with what I'm doing. He doesn't want to get involved in it, nor do I want him to (just for the simple fact he is my boyfriend, not my husband and he doesn't need to have a hand in anything that I'm doing business-wise). He's there for moral support and will help on specific tasks if I ask him to...but I'm the one running the show, he's my cheerleader!
I have a few contractors in mind. None that I have worked with before...but I have been eyeing them. That's definitely something for me to keep in mind. I generally have an obvious "no nonsense" attitude that helps me to weed some of that out...but I will definitely be observant when dealing with them.
Great advice, thank you!