The idea being that he would eventually bank enough money to start contributing to the subsequent properties. 

Dont use certified funds for subsequent months for this specific reason, if the check gets lost, the person is out those funds for a very long time.

As with many things in life and history, those will more experience and tenure are more often better predictors of outcomes.As for the OP and subsequent responses, I feel there are a lot of good points posted by many.

@Anthony Wick I had the same concern you did about not paying EM and your subsequent reputation.

My impression has been that if the Bay Area falls significantly, then most of those other hot markets drop quickly behind it.So, if you were someone with absolute perfect timing, maybe the optimal play would have been to get out of the Bay Area a couple years ago, to continue riding the perfect wave upwards in markets that are now outperforming us (and subsequently getting out before the next correction).

Subsequently, I'm interviewing the 3 "Guru.com" applicants via their profiles on Upwork where they've been adverting for much lower rates.I'd be interested in other members experiences and similar comments.

A divorce and subsequent short sale of the marital home tanked my credit then a job loss added a ton of debt making me unattractive to banks.

I think any subsequent tax bills you pay instead of the owner is at the same rate which won the lien.

Once you check it (or un-check it), it should stay that way for all your subsequent posts & replies. 

In your situation, it appears you will be owning your subsequent home so you would not be able to use this strategy again for the second purchase.