I need some advice but also some sense talked into me.
Little background: I had a '99 chevy Silverado with 215k miles but wrecked it right before the turn of the year (single car accident, totally my fault, I'm fine). Drove it home and drove it until got insurance straightened out - but once the body shop started working it quickly got totaled.
So, I'll be getting ~$4,600 from the insurance company. (Yes, I was over-insured, but it paid off)
Time to buy a new-to-me car. And that is where YOU come in. I need your opinions and advice. And I just need some mustachian folks on my side because everyone else is saying "buy something nice, you deserve it", etc.
Needs: 1) tow a boat - non-negotiable - main hobby (so truck, SUV, van) - 20 foot bass boat - so not a little boat to tow
2) reliable
So two options that I see (not saying there aren't more): the price bracket of 10-12k, get a truck with ~100k miles and hope it works out for 7-10 years. Or, spend 20k to get a 2-3 year old truck with 35-50k miles and drive it 10+ years
Financials: salary:75k , investments: ~60k, age: 23, cash on hand: 5k
Goals: FIRE early (more than likely, take a year sabbatical multiple times along the way). Also hesitant to take on debt, so I could quit my job easily and hike the AT (or something crazy)
Driving: currently 10 miles round trip to work (trying to get to biking)
More than likely will be moved locations for work within 2 years
Pull a boat through mountains and also long distances
Decent amount of highway driving to go on trips
What would you do? What should I think about?
Drop your wisdom on a young guy making his first adult vehicle purchase