Which Major Urban Market

[Maxwell Lee]

My wife and I have done a fair amount of investing in cheap cash flow markets. Aside from two condos in NoVa, the second of which was sold earlier this year, we have no experience in high appreciation markets. We wish we didn't have to sell them, particularly the second one that was ideally located by a metro station in Arlington, but it was probably necessary. 

Anyway I'd like to be able to get back into a similar market for the simple reason that a decade (or more) from now I'd like to have a property in a desirable, urban neighborhood of a major American city. I'd love to have a place that we can live in, or at least vacation in, if it makes sense as an investment. That's the key. If not, we can always just rent. But boy would it be nice to find something that we can get in on early and enjoy when we want to for many years to come. 

So what kind of market/neighborhood am I talking about? Imo, today, I'm interested in NYC, Boston, DC, San Francisco, Los Angeles, Chicago, Philly or Seattle. A vibrant, walkable neighborhood in a diverse, cultured, major metropolis. (Yes Seattle is a bit borderline and kind of is a gateway to the next tier) What kind of property? Really anything is fine as long as it fits into the type of neighborhood described above. 

I'm assuming Chicago and Philly are my only realistic options for finding a sensible long-term hold...something that isn't already overvalued, overheated, and can possibly cash flow. But happy to hear any thoughts from anyone who has experience in these metro areas. Also open to thoughts and speculation on cities that could become what I've described. Thanks!!