Maybe make a fake account on an IP address you never use if you want to do such a survey in an area you're interested in.I don't think that legislation is a huge issue so far - there's always ways to sidestep it, etc. and they generally are not enforced (unless under HOA which most newer homes are).

He tells me that he has a lender who promised financing for upto 5.5 million (to cover holding cost), but the land has to be brought clear of any lien.

He may just be blowing smoke, as is his usual deal-closing behavior, but he has come through on every promise he has ever made me.

After completing that formal endeavor, I promised myself my next pursuit would be purely self-taught and FUN.

Let's talk about a lowball offer case.Property is listed for 100K ( might be an overestimate from sellers part - seller/agent).Based on your calculation as an investor you comeup with an ARV of 65K.As a investor you clearly think the seller will take this as an lowball offer.Will you still go ahead and submit the offer for 65K or won't submit any offer and wait for the listing price to come down.( assuming your agent also agree with valuation and submits your offer) Assumption here is the investors ARV calc is right 90% of the time the property should sit in the market for a while without any promising offers and listing price should comedown.

Without the promise of appreciation though, I dont think it is worth the headache.

It sounds promising.  

(Last thing, I promise haha. 

What questions should I ask, or how can I tell if it is a promising opportunity?

The ARV is very promising at 350k The owner is willing to finance 50k.There is a previous owner financing for 100k.