Real Estate Investing is a daunting challenge that I feel at time is too idolized. 

How should I approach this ahead of PSA?

Instead of a 90 day challenge its more like 180 day challenge, but for my first one that's ok.

I guess transparency with the lender is the best approach, like you said.

I do hear load an clear it's about the people you work with - challenge is how to find those people - the people you can trust. 

We are currently building a few spec homes but finding finished home lots is very challenging. 

If you were starting today, and lived my nomadic lifestyle, how would you approach real estate investments?

Investing while renting is actually the best approach financially.

I had never heard of "house hacking" before, but it was mentioned in the first episode I listened to, and knowing that was already the strategy in my head, I figured I need to learn all I can about this approach!

I'm considering approaching the lender about a deed-in-lieu-of-foreclosure, given the 7-figure difference between appraised value/loan balance, I'm hoping that would be a solid last resort.Keen to hear if anyone has been through a similar situation and whether there's any other creative solutions I should consider.