I tried RE Investing many years ago before the internet and miraculously did not loose my shirt but broke even on one house and due to other circumstances was forced to walk away from another.

I cannot see a scenario here where he is better off re-levering to enter if he can't weather a shorter time frame; and if he can weather one, then he has the funds to put a downpayment outright on a  2nd.

We host RE meet-ups as well.

RE investors do this type of structure all the time (though most don't house hack).

Especially CA folks who are so in tuned to RE and owning RE as you know look at all the CA investors that flock to the mid west and rust belt to buy rentals.

(For a lot of gurus, the education is just a top of funnel entry point for them to then have you find deals for them, invest in their deals, etc)If they are active in real estate themselves, I would ask how much they are making from their RE versus their courses?  

But i was able to achieve the elusive infinite return on a majority of my RE and all of my investment RE that I purchased prior to 2020.Infinite return has the benefit that the finances are not the hindrance to scale.  

RE is a very a depreciable asset.

Quote from @Dave Allen: I'm in a bit of a situationMy wife and her parents are selling a duplex they own together.My wife is trusting me to re invest into cash positive investments.We could stand to take as much as a quarter million, and tax free since we lived in the property 2 of the last 5 years.What are some suggestions for markets that would provide cashflow?

Obviously, the at least 42 input variables can be adjusted to your own risk tolerance, but this is far easier/quicker than to re-create the entire input.You can find the link on my profile page.