But I'm curious if there are any desirable markets that are becoming more affordable.

I live and invest in Brooklyn, so what I say is only applicable to here though I imagine it probably applies in the more desirable areas of Queens (Astoria, LIC, Woodside, Sunnyside, Ridgewood, etc) as well.Basically, at your budget, what you're looking for (living rent-free within 30-45 minutes of Manhattan) is not going to happen -- at least not in Brooklyn.

I don't know about you (or John Underwood), but I neither have the time nor desire to search thru tens of thousands of county websites and hard to read excel spreadsheets to find what I'm looking for. 

Here are some reasons I believe the values are poor 1) lot more home owners than home investors 2) if an owner wants an ADU they can easily add one that is exactly what they desire.  

This allows tourists/snow birds who are visiting to also rent a boat and keep it for however long they desire because they can dock it behind their vacation rental.If you have any questions let me know.

Their desire to lend on investment properties teds to vary from time to time so you need to keep in touch.

Which often times consists of people having the desire to purchase but not the means to.

This way you generally can refi or sell and 1031 at the time you want that is optimal versus a short term loan where you are forced to sell or refi on terms in the market you do not necessarily desire.  

I'd recommend going to some REIA meetings and see if you might be able to find some partners with properties in desirable locations that could be prime vacation rentals.

I own a 3/2 in a desirable, middle-class neighborhood in Houston.