Your Checkbook 401k could invest and obtain a non-recourse loan to finance the investment - in which case you would have to avoid any "prohibited transactions."

Now, in '18 with 1 rental, he says 62 yoa in '19, if no earned income (to avoid tax on SSA.

I am in central WY, but used to live in Rock Springs. 

What are the typical issues that you've encountered and how do you avoid it? 

If you buy the house jointly, in a trust, you can avoid a lot of needless complication. 

@Kevin MartinSomeone once told me tax deed auctions are like cutting down a tree.. 95% sharpening the axe and 5% cutting....means do your recon...check public records and property appraiser...avoid ones with 3 or more listed owners in property appraiser.40% get redeemed.Dont trust Google street view...do a driveby..break inside if needed...check them out!!!

New Central air and heat in duplex.Asking price is 69,000..

If you do sell though, avoid Nov-Dec, and wait for the Spring market. 

We currently own a new house that was built before we moved in, and it is in a developing neighborhood, we are going to rent that house out then move into the house we just bought and do a live-in-flip and possibly sell or rent after two years to avoid the capital gains tax on the profits.Our goal is to get as much stuff done to the house as we can before we actually move in because we have two small children and it will be rough trying to live in construction zone with these two crazy babies.So, so far we have taken out the whole kitchen, removed ugly tile in the living room and two bathrooms, and started demoing the laundry closet.

You should consider avoiding 50-50 as it can lead to deadlock without an easy mechanism for disputes.