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Particularly if you enjoy the area and could see doing your business there, I recommend the low-money-down house hacking route (#2).I think if you can manage your personal expenses and make sure to get renters in your extra rooms, you can use the rest of the money to launch your other investments.

I enjoy working with homes, whether that be through helping to buy/sell or fixing up.

.$322.83/month Principle and InterestMonthly Cash Flow: $8.97I know This isn't a great cash flow deal, but I would essentially break-even until the property is paid off in 10 years if I held it as a rental.The other scenario, which I am leaning towards is to sell to an owner occupant with a wraparound mortgage.I could increase my cash-flow substantially, get a decent down payment, sell for a higher financed price, charge a much higher interest rate, and enjoy less management headaches.If I sold on a wrap I could sell for $39,900$5,000 down (tax refund time soon :)$34,900 amortized for 15 years @ 12.75% Interest = $435.84/month PIThis would allow me to make money on the front end ~$4,000 and make $133/month cash-flow.I could also play with the numbers a bit to make a higher IRR, but this seems like a doable scenario.Would you buy this?

But I usually sit in the 20x20 room off the kitchen watching the sunrise & lamenting the 1.5 hour drive I once did for a 9-5 JOB.

I just separated from active duty as an intelligence analyst and decided I wanted to do something that I enjoyed, not just something that was an easy paycheck.

Watching your mortgage payments get paid by someone else is always a good motivator (becoming a landlord brings its own challenges, but it's one of the easier strategies to explain).I wish you the best!

Enjoy as you prosper.....

I'm currently watching several of there projects to see how they sell.

Now you get to enjoy reaping the benefits.