Other factors like the duration of the project play in heavily in this analysis and development is notoriously difficult to predict the timing of and to account for life's uncertainties.  

The NWI classification means absolutely nothing from a regulatory perspective and is notoriously spotty in accuracy, but it's a good first hint that there might be something there to look at if it shows a feature.

So I know that the Los Angeles area is notorious for being "impossible" to cashflow.

If that is the concern and the threat of prison is not deterring that behavior, I don't think the threat of losing a state license will be effective.My partner is from Illinois.

That to me is a prison sentence that I'm trying to escape now.

The Villages is well-known (a bit notorious, too).

Don't box yourself into a prison, stay flexible. 

FHA loans are optimal for 3- and 4-units specifically because conventional loans (as I understand them) jump up to 15% down for those assets, while FHA loans are still feasible at 3.5% down.FHA loans are notorious for being cumbersome and I've had some clients miss out on properties because of the loan, but when you're looking at a 3-4 unit the buyer pool is largely looking at the same metrics (cash on cash, ROI, etc) and that levels the playing field significantly. 

@Kelsey Gabhart many real estate investors are aware that Zillow is notorious for inflated values.

Again, this is a business, as long as I am not worried he's going back to prison soon (he's been out and renting an apartment for a couple of years and now wants to rent a house), and he has a stable job that pays enough that he can afford it; then it's not my job to judge him or his employment.