The challenges we found were that:Even in a great town like Greenwich (Fairfield in your case) the multifamilies are in neighborhoods that were not desirable, at least not now that we have kids.Multifamilies are expensive in an expensive town.

The most desirable areas always have the highest real estate prices.

Now figure out your desired profit.

I was under the impression that in general, for single family home rentals, having better school districts would increase the desirability of the home for families. 

You may be in a "desirable school district" but if the school itself isn't desirable it defeats the point.

He has no desire to give up his teaching career anytime soon. 

My children are certainly my motivation, so I understand your desire to make it a little easier for your loved one's.Thanks @Shiloh Lundahl. 

I don't understand your desire to knock down an existing property and build from scratch.  

We just don't have the desire or time available to flip.

Not to say avoid like the plague, but if you were looking for A/B, Euclid and the Randall Park area may not be desired areas for that.