What is the current market valuation of the property based on comparable sales (defined as similar properties, within a 1-mile radius, within the last 30 to 180 days, that are within 10% of total square footage)? 

Quote from @Adam Macias: Wholesaling as it is today will be a thing of the past.It’ll truly be strange to even hear people and gurus trying to make big money off it.The more people try wholesaling but then end up not having an end buyer or cancelling contracts or trying weird things like novations, the more all of real estate will be regulated and cause requirements like licensing to be able to transact more than just your personal resident purchase.Which I don't know why hasn't happened sooner.Here's all the states (in red or yellow) requiring a license to wholesale or at least have started the process:Credit: REITipsterI think licensing and regulation is a beautiful thing that should happen if you plan to be an wholesaler and do more than one deal... which is going to be the case for anyone taking this business seriously.Or even it being regulated to need a real estate agent to do more than one deal outside of buying a personal residence.I've had plenty of failed attempts with agents in pursuit of wholesale deals and I know exactly why, it's not because the agent couldn't find me deals, it's just not practical to think there's opportunity for the numbers a wholesaler needs to make a profit on top of everyone else needing to these days.Because the only sellers who truly can sell at a deep enough discount are usually those who ran out of time and just didn't do something sooner with their situation.I know many coaches and gurus will disagree with me but there’s no regulations on youtube gurus and what they teach either.If we look at the current state of the market in hot cities, the availability of online resources to the average homeowner, how many deals can you possibly believe are available at 70% of ARV?

It will happen in red AND blue states.Why?

Of course it is a red flag!

Just factor in a little time and effort to get everything squared away, and you should be fine!

And are there any big red flags that make you walk away from a deal right away?

I would be so deep in the red.

Would you have any recommendations, in your experience, for what to look out for in the documents that would be red flags or items that would negotiable?

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

The 3 issues you described are all fairly large red flags, especially for someone's first property.