Probably like your friends I would prefer the 2 family place as a launching point but would settle on a townhome in a great school district once the kids are of middle school age.
We did an excercise as part of my MBA program that initially framed a scenario for a winemaker to make all of one type of wine or all of the other ans asked which way to go.
Funny but ther were a few in the class that argued that perhaps there was a third alternative. Rather than choosing betwen the scenarios why not proprtion the grapes to make both wines.
Learned a lot form this exercise from the simple standpoint that there can often times be different objectives. For some such as the JWM’s of this board in might be profit maximization. Try and time the market. Might be righ or might be wrong. For otehrs it might simply be to lower the amoutn of risk. Buy it when you can, create forced savings, pay it off as fast as you can, live debt free. But there can also be hybrids or the scenarios.
Most of the posts here throw up so many blanket statements without considering that objectives can be different. Therefore the desired outcome can be obtained in different ways.