Suggestions? What would you do?

[Joel McKinney]

Long story short (as I can make it):

I'm 39, still trying to get my life in order.  I have been enlisted in the Navy for 7 years.  The opportunity to pursue becoming a Navy pilot has recently presented itself.  I'd be making ~$80k-$140k/yr for the rest of my career and have a good retirement in 13 years.  Flying is my dream, and I got a bachelor's in it, but never had a job flying.  The Navy keeps me away from family WAY too much and we'd have to move every 2-3 years, worldwide.  Civilian aviation pays peanuts for the first 5 years, FYI (~$20k-$40k/yr), and once pay gets good, it'd keep me away from home just as much as the Navy.

On the other hand, my wife is a successful real estate agent of about 4 years and is opening her own brokerage (the Navy would make this near impossible to sustain).  She has suggested that I could become a loan officer or contractor, and has connections who could train/hire me.  We could bounce referrals to each other and potentially be very successful.  Neither seems very interesting to me, but I'd be able to stay home with her and my 3 wonderful kids, I could still serve in the Reserves, could MAYBE fly on the side if we become successful enough, and I feel it could really help us become successful real estate investors.

We currently have one decent investment property and have done one decent flip.  I have been wanting to aggressively grow our rental portfolio in order to achieve financial freedom for the last few years, but my wife is very pessimistic/conservative, wants to focus solely on paying off ALL debt first, and hates the thought of even acquiring "good" debt.  We're both stuck in the rat race, but have different strategies to get out, but neither of us thinks the other's strategy will work...  As much as I love aviation, I think working in the RE industry would expose me to a lot more possible opportunities that could help change her mind and align with my financial freedom goals.

Thoughts?