They are living in an illusion of material success fueled by a mountain of debt.

I don't know (recall) if they are in local ordinances but I do recall vaguely seeing some legal / ordinance type of material detailing when it can and cannot be done, regarding building in a way that directs water towards a neigbors property.I don't know Chicago that well, but as a homeowner I would try calling your local building and permit center and see if one of the local inspectors can direct you to the code section to read.I'd do that before anything else because knowledge of those ordinances will arm you / prepare you best to approach the other parties.With regards to the possibility of 'dealing' with the water, I'd be thinking about ways to do that, too - in the event that the above / negotiating an alternative solution is not fruitful. 

The alternative is that interest rates do finally begin to rise, which puts pressure on all of the companies that are overleveraged.

What are my options or alternatives?

I agree there is only a subset of estates where this might work; it will not where the heirs are unwilling to wait, if there is significant debt, etc.I am not interested in deals where I have to acquire the property outright; I am trying to come up with an alternative method.

Problem numero uno is that too many people are going to college just because they think the diploma is the value and they don't have a particular desire for a path of learning to grow.Problem B is that too many people go into debt to get a college degree when other alternatives are present. 

Sethi believes the following:After inflation, the average return on owning a US residence is zero (Robert Shiller stats)Most people don't factor in the true cost of owning a home (interest, taxes, insurance, maintenance, cap ex, sales commissions)There is a lot of work involved in sourcing and managing rentals (vs alternatives)The masses will not have the perseverance to properly purchase RE investmentsIndex fund investing is easy and provenHe is right on many fronts and is speaking to the masses. 

The thing is I never really get an answer as to where I should be looking for the best options as an alternative.

As an alternative to hard money, you could try to ask for seller financing.

If you're wanting to stop self-showings, open houses are a good alternative as mentioned.