If you have the money and you can do something with it in California and you trust that the money will grow more there, then that's what I would do 

Then keep the speed of money & time moving to make more money in the end.

Find the money and find the deals.

second was Hard money it was legal then. 

We put back most of the money back into our business, as the cost of living for me is covered by the student rentals.

She'll pay me market rate rent, thus keeping that money in the family, and the condo will eventually transition into a more traditional rental property that will support my retirement and that my children will one day inherit. 

There might be some confusion around the 60-day rollover rule which allows you to move money from one IRA/401k to another (both pre-tax and Roth).

I don’t think an app is needed at all, save the money.

I’d keep it, do a little cash out refinance if you wanted to regain some of the $, and just rent it out or STR it and make some money on it..Appreciation always goes up, and a few years down the line (and/if interest rates come back down you could pull even more $ out Tax free!)

You should factor in time value of money and opportunity cost.