Sure it might be useful but he/she is not going to reveal any real goodies anyway; you need to uncover everything, the  good and bad, about the building and the finances for yourself.

But if you have an LLC, and nothing else to show up as your assets (because you used land trusts to give you a layer of anonymity and a simple search is not revealing you are owning many other juicy assets) an ambulance chasing lawyer working on contingency will see a small target on your back and hard to get proceeds from victory in a lengthy lawsuit and move onto easier paydays. 

Could it be that the purpose of allowing the original owners to remain as sole beneficiaries of the trust was to avoid revealing the price paid by the trust for the property?

What this reveals, is that even with the SAME criteria, there are deals/properties that will appeal to some investors and not others. 

You can then refinance through a Non-QM product as well all without showing a job, revealing taxes, or pay stubs.  

Further investigation reveals the owner and his wife had a joint Ch 7 bankruptcy that was discharged 11/08.

Without knowing those answers, I can't decide what is the best action.Since the county has already decided upon the road improvement and accompanying assessment and presumably you will reveal this to a buyer, you already have incurred any "loss."

But, furthur inspection reveals rotten deck underlay.

Would it not make more sense for me to estimate a number the owner would counter with, then subtract what an inspection would reveal with respect to things that need to be repaired, and providing that information along with my initial offer in order to justify my calculation, rather than submitting something to my landlord that looks like someone just made a random offer?

No , actually some research into his background reveals very limited success - until he wrote a book on success!