My wife worked out that way previously and we still have fond memories of many places we visited with Sedona being one of our favorites.

But there is one exception to this. 

Directly withdrawing funds from a Traditional IRA before the age of 59½ typically results in taxes and penalties.However, one option to consider is using a self-directed IRA.

If I did it, and I'm no one special, anyone can do it.

For your $240K new-build townhouse, a cost seg may make sense if the tax savings outweigh the study cost (~$3K–$6K), especially since you plan to hold it for 10+ years and can benefit from immediate bonus depreciation.For the $380K older townhouse, cost seg with look-back depreciation could provide significant one-time deductions for missed depreciation over the past six years.

You and Him are filing one joint tax return. 

Listening to one bigger pockets episode or a good book here and there really can be a good reminder, refresher on the financial journey.

Personally I'm against these types of programs, especially 5-figure ones.

If you plan to buy in your hometown, buy a 2-4 unit, and live in one of the units.

I can always hire property management for these, but there aren't any really good ones in the area that I'm investing in.