Dumbandjobless. wrote:
My biggest question is more about getting in "true debt". You know where every month after bills you are in the red.
Ok, so what you're describing is cash flow... specifically wanting to avoid negative cash flow. If you use that term instead of misuing the term "debt" you'll avoid confusion in the future.
Now, on to your real topic.
I think it's wise for you to skip the big-paying jobs if it's not what you want to be doing, and you feel they'll consume your life and make you miserable (bad boss, etc.). A lot of people fall into that trap, and never leave. Or, plan on leaving in X years, and then get stuck, or lose their health in the process.
You are ahead of the curve.
The lifestyle choices you make will determine what you need to make at a job. If you really don't care much about material crap, or keeping up with the Joneses, then you can easily live well on a lower salary, or a high-paying gig where you determine your own hours.
Two red flags come to mind though. One, the $10,000 engagement ring. Think long and hard about why you feel it's necessary to spend that kind of money on a ring. Is it to impress her? Impress others? Is that kind of thing important to her? If she values that kind of stuff, then she might not share the same values you seem to posess (money not that important... not materialistic, etc..), have different expectations of what she wants out of life, etc.. $10k for a rock is a slippery slope to the luxury cars, luxury homes, private schools for kids that require the kind of jobs you've left/passed up.
#2 - Buying the townhome. You'll likely be married in a year. Is this the kind of place you'll both want to live in? I'd be wary of locking yourself into a purchase when you have the uncertainty of 1. upcoming job change, 2. marriage. Lots of variables, and flexibility could be worth quite a bit.
Why can't you rent a 3-BR townhome, and still collect rent under the table from your buddies?