It's conceivable that these neighborhoods might not be affected at all in a downturn that does affect other (less desirable) neighborhoods within the city.In fact, I think that historical data shows that this occurred in the '08 downturn --generally speaking, a lot of the higher income A grade neighborhoods were minimally affected or not affected, while the lower income neighborhoods got hit hard (another example of the "Matthew Effect" where the rich get richer, and the poor get poorer).As they say, "real estate is local", and "location, location, location!"

My market (Milwaukee) has gone up barley double digits, so we have appreciated just over inflation, there is no conceivable reason for prices to go down.

If you could realistically sell your first example for $70K in under 90 days, you are talking about a different market than what "Sub$30K" evokes.In our market in northern Utah, the typical problem with 75+ year old houses is not the original construction, but all the ill-conceived home owner improvements since.  

There will always be methods to create money if you're creative in every conceivable market.Go ask the 30 year veterans of this business.

After all, it's conceivable to do a bunch of flips for the sake of notching a dozen of them, but is that the proper focus?

Yes you would have to refinance the commercial loan in 5 years most likely but you could conceivably keep adding cash flowing properties onto that original commercial loan whereby it would be one blanket loan and you would only have one payment.

The option money along with the security deposit should cover any conceivable damage even in a worst case scenario barring him intentionally destroying the property.Please point out anything I might be missing or feel free to just tell me i'm an idiot for even bothering with this guy.

They seem to have closed just about every conceivable loophole, which leads me back to trying to get licensed, rather than operating on the fringes of the law which could be changed at any time.  

Yes, I know “if you can conceive it you can achieve it” and “always think positive.”

If you're in a decent sized market, it's conceivable you could hit your goals.