Realize the historical appreciation realizing it goes in waves (so short term depreciation has occurred but the long term appreciation has for over 50 years surpassed inflation and virtually every other market). 

Close in neighborhoods like Charlestown, Jamaica Plain and Fenway have too.As to what gentrifies next, I'd look at historic high-crime areas in Dorchester, Mattapan and Roxbury. 

Inventory is at a historic low and the average sale to list price has been above 95% for over two years. 

As I recall Mammoth can be a feast or famine historically but some of those dymamics may be stabilizing.  

Just today, I used BP's rental tool, pulled closed sales comps and historical rental data for a "prospect.

In this scenario, I'll say I'm "asking for a friend" who is looking to move on immediately and retire.Say for instance you have an older historic house that's paid off and you've been using this to operate your business out off.  

how do you know what you're payments are going to be like long term (assuming most comes from commissions) .... you don't have enough historical data.

It's an area where some students may live there but historically it's not considered a good area.

If you are expecting to sell or exit in 5 years it might not be enough of a timeframe if there is a downturn ... but longer term prices have gone up historically in areas with strong economies like you said .

Historically, very few times have people taken a beating on real estate.