Also, seeing nice round numbers is always a red flag to me, it shows me that more research is needed.

The one red flag I think I see is that he is breaking his 24-month lease after 18 months.  

Once it is re-rented do a move out letter itemizing your costs and bill them, but don't expect much.We have a strong non-refundable holding deposit, and red flags should be going off as soon as they fail to hold up their end that early int he contract.

The fact that the realtor didn't understand basic Bay Area pricing strategy is a huge red flag.

No different the the medical opinion that says a bottle of red wine a day is good for you and another list that says that is bad for you......wait, maybe that is a glass of red wine :)A list is just as good as the next list that says something different.

One even told me that the government won't allow conventional loans of less than 50k because this causes a red flag with the closing costs being such a high percentage of the loan value.  

I think it's a bit of a red flag that they want you to hit the seller with payment of any kind.

Look up wedge-it's or redheads  probably cost 30 bucks for a box of 50 1/2"x6" and alls you need is a hammer drill or if it a basement or crawl then a 90 degree angled hammer drill available at most tool rental stores.These 3/8 ones will work alsohttps://www.zoro.com/red-head-wedge-anchor-carb-st...Tom

I don't know the totality of the circumstances concerning your deal, but if the Seller is prohibiting contractor entry which falls within your inspection period, that's a big red flag to me as an investor AND a contractor.

Red, I guess it depends, What type of deal is it?