My concern is that there is a lot of risk for the unknowns.Does this imply that I would avoid the purchase? 

Mortgage also typically being fixed implies that cash flow typically improves fairly fast but if it is negative $1k/month or more (I have seen many purchased that if purchased with high LTV would be this negative) it will take time for it to become positive   Second best advice is do not believe other people’s under writing.  

You also described them as an investor, not a successful investor.In the current market buying move in ready property with conventional financing at high LTV is not going to generate good cash flow regardless of what RE agents in the Midwest may state/imply. 

It is showing the search engines that everyone prefers you over anyone else.Engagement doesn't  imply people liked the site.

Regarding the shared driveway without a written easement recorded: if it's his only ingress/egress to his property and he has been using it for a long time, he may have what's called an implied easement at this point (at least that's what it's called in my state, laws are different in every state).

And are you implying that alot of these now-high-priced properties that won't cash flow are being bought by corporate investors?

For bigger companies that feel they can take the risk more power to them but to imply that a business that does require one shouldn't be trusted is just silly.

We were left with conservative lenders and lower new housing supply.It is also worth considering that the word "crash" usually implies sudden, like a car crash.

Not implying anyone who has tried to help is insincere or has mal intent.What the OP wants is immediate relief from the anxiety of a situation that merits a thorough discussion with a qualified CA who will ask the right questions.

Generally, a title insurer does not show a chain of title to the proposed insured nor does it say or even imply that the property is being conveyed free and clear of competing interests.