But from the reports I've read, a ski resort is more insulated (not free though) from declining snow pack at higher altitudes (so you can keep that in mind).

But even there, the county commissioners are hearing from first-responders that short-term rentals are responsible for a higher percentage of emergency calls -- out-of-staters struggling with altitude, dumb people popping too many edibles and freaking out, etc.

I can't say that me myself, have reached "cruising altitude" and am on the beaches of Bali. but I can say that things have become easier over the years and when you have done over 100 transactions, the next one becomes satisfying but less and less of a big deal.

My situation feels like a 747 with engines out, trying to maintain altitude.  

The places I'd recommend looking are Brockton, Taunton, Middleboro, Plymouth, Fall River and New Bedford - the latter two being south coast, not south shore.For example, average 3-plex sale price over the last 6 months:New Bedford: $208.3KFall River: $231.2KTaunton: $321.2KMiddleboro: $382.6KBrockton: $444.3KBoston: $974.6K.Not only do you get more for your money on the south shore, but as you get north of the MA Pike and west of 495, you're into the Worcester hills - about 1,000 feet in altitude. 

If you do go, it's because you have a sick relative somewhere who needs to see you before they go on to glory -- the best kind of story for that is an expensive one, like a blind half-brother with a rare blood disease who is only free of constant pain in this one remote high-altitude institute in the Cascades...something so outlandish no one would make it up that at the same time implicitly explains why you need the rent checks to be on time.

Do you get many nose bleeds at that altitude?

Ski during the daytime . . . networking and meetings in the evenings . . . high-altitude drinking at night.Anyone down?

The Worcester hills are at about 1,000 feet in altitude. 

Very Progressive, and somewhat green.I was in Colorado at 9000 feet and loved the altitude, so BZN's altitude works for me.