Long time MMM reader and forum lurker (since mid 2012). I apologize in advance for the long text, and for asking yet another what-should-I-do car question. I feel like I've made 8 years of bad car decisions and I need some advice.
Back story:
Jeep 1: In 2007, fueled by the $1000 cash for clunkers thing that was going on, I traded in an old junker for a brand new Jeep. Of the $23,500 purchase price, I financed $22,500. After 2 years of making $369 monthly payments, a windfall allowed me to pay off the loan balance. Awesome. I then drove my paid for Jeep until January 2012 when my Jeep was totaled when I was hit by another driver. I received check for $18,500 for my Jeep. Time for a new car.
Jeep 2: Long story short, I put most of the $18,500 down on a $40,000 bigger Jeep, which I kept for about 3 months, before selling it back to the dealership for $35,000 taking a loss of $5000 principle plus another $4000 in tax, title, license.
Scion xD: So, right around then I discovered MMM, and his list of cars for smart people. Thinking I could then finally act like a smart person, I put $8000 down on a brand new 2012 Scion xD and financed the remaining balance (around $9000). The only problem was, that I hated the scion. It felt cramped and cheap. So, since I am a homeowner, I talked myself into "needing" a pick up truck.
Truck 1: Not wanting to be totally unmustachian, I bought a used 2007 truck with about 77k miles on it. Traded in the scion (got about $6000 equity) and financed about $7500. Kept the truck for a while, until I found out I had a child on the way. Then I figured I needed a bigger truck...
Truck 2: Brand new 2014 double cab, off road truck. Price $29,500 (plus tax title license). Traded in truck 1 and ended up financing about $21,500. Payments are $335/month. I now owe about 20,500.
Where I'm at now:
I hate having a $335 truck payment. Every month I think about how I could use that money for something else (max out roth, pay down student debt, etc.) So, now I am back to thinking of getting something off MMM's list. Perhaps a used Mazda 3. So first I think, okay I have about $8k equity in my truck, I'll buy a 2006-2009 used one with 95k-100k miles (that's what's available at that price in my area). Next thing you know, I'm thinking I'll just get a 2011-2013 with 30k miles for around $12-$13k (putting $8000 down) because $100/month is better than $335, plus safety/reliability (since I have a baby), and likely there will be some factory warranty remaining.
I'm just not sure what to do anymore since I feel like I keep making the wrong choice, and have wasted so much money the last 8 years on cars. Another issue is that my wife is (understandably) frustrated at my car hopping. We bought her SUV new, back in 2005 (for cash) and she still drives it daily.
Any thoughts/advice would be greatly appreciated!