harm
+1y
I know I have basically no reputation here, no real leverage in conversation, but you've got this all out in the open right now.
I've had the parents' debt issue before, and I agree with NYTRDR - family first, ESPECIALLY when it comes to debt. You have to give respect to get respect, right? I paid my family back with every spare penny I had after they helped me out - and I worked off the rest of it at the family business. My brother bought Dad's old truck from him, and took years longer than he should have to pay it back. You can guess who is more likely to get another loan/help (in my family, though, he's got the great career and I'm still poor. haha). Also - my parents haven't given me a hard time about finances since I proved (to them at least) my responsibility.
You will miss your truck every day of your life if you sell it after putting this much into it. You ever see a vehicle you used to own (and didn't hate) driving around? Could you stand to see some douche driving your truck someday? I couldn't, and my truck is kind of a pile of shit. It's going to the scrapyard in pieces before I'll sell it.
They are giving me a hard time about the free ride I gave my ex-girlfriend for the past three years plus, now that they found out. Just throwing that out there, because I'm giving myself just as bad a time about it. I've had three relationships where I've been the provider - one irresponsible debt-laden self-absorbed.. yeah.. - one who was just between jobs, not her fault, but I'm a good mark - one who thinks the feminine movement is bullshit and women shouldn't work so long as they run a household. Tell you what. If I have to vacuum, you have to pay rent. From now on. lmao.
Relationship advice is the hardest kind to take objectively. Do what you feel is right, but always think about what you're doing in a relationship!
The caddy. Man, when I was looking for a daily driver I ended up spending 4 grand. the car broke down anyway and I don't have the money to spend on fixing it because I still owe on the damn thing, plus insurance on a newer car compared to an older one. I could've put 1200 bucks into a crappy old (perfectly running) toyota, 1200 bucks into fixing it up, and still be at half what I've paid on my car.
Personally in your situation, with my history, I would sell the caddy, find a cheap, reliable daily driver, with good gas mileage being hugely important, pay my parents back, use the gas mileage to visit the girlfriend every chance I got.
As for the truck - take your time, you have so much invested already. just keep it tuned up!
/rant