Welcome and congrats on putting your purchase criteria down in writing, you're a step ahead of a lot of investors.

If your net, after-tax return is better than other investments the IRA could make, then you have come out ahead.

Spirituality helps me, I don't know where you stand, either way have faith in yourself. 

I have some work ahead.

You're a bit ahead of me concerning the rentals, hope to be closing on my first duplex soon which is exciting. 

I do it by planing ahead and if you have nights booked as far as 6 months out you can get higher rates and then all you have to do is lower the rates in gaps between bookings about one month before the date.

I think 35k to 40k makes more sense for the job you have ahead.

And, heck, with your contracting, flipping, appraising and real estate experience...you are already WAY ahead of the learning curve.

Life circumstances tend to make that sort of arrangement less viable as you get older, but it's a commonly used method for younger people to get ahead.

If you break even or come out ahead of the game, I'd say its safer than not.