Gutting an older house often reveals many many more issues and costsGood luck and it does look like a very cool house !

Just because the roof isn’t actively leaking (honestly the condition is so bad I would be surprised that it isn’t but I can’t prove it as my inspection was done on a dry day and the attic is “finished”) I have already compromised on a lot of the issues that inspection revealed and refuse to compromise on this.

Ditto if you can show that the seller's agent knew about the seller's deceit and ditto again if you can show that the home inspector could reasonably known that there was a wet basement and didn't uncover and report it.I think the seller would be in an especially weak position if he filled out a disclosure and did not reveal the issue.I'd start by documenting everything you can and then talk with a real estate attorney.BTW, the smell of a wet basement is pretty obvious. 

I know the bank will also be a 2nd pair of eyes, but we have had plenty of deals after the bank is ready to close and we end up finding something that is reveals the deal is not worth it or misrepresented.

The home inspection revealed severe insect infestation, broken windows, and damaged masonry, plus there is a makeshift set of stairs leading to a loft.

The rent associated with the ADU can be tempting, but typically is a Lorelei that is revealed if you do a thorough pro forma.Good luck

I read an article on negotiation, and it said never reveal what you are willing to pay for a property first.

Or my end buyer to waste money on a title search that reveals a lien, judgment or undisclosed co-owner that kills the deal.In my market, it doesn't matter much what type of property it is.

The agent is trying to avoid any other offers being submitted that might be higher than the one from the "intended" buyer, thus "not available yet, don't have keys yet, etc," Of course the agent can't reveal this to other agents/buyers.

I don't think a lot of people know about this yet and I expect it to bring even more appreciation to the area.https://www.researchtriangle.org/news/developer-reveals-more-plans-for-250m-seaboard-station-in-downtown-raleigh/