IMO, I have always felt there are two broad types of DPOs, not well differentiated by most dealers or post office lists:
1. Those which were actually closed such as (apparently) Portsmouth Grove, RI, typically for lack of business; but also for conversion to an RFD, creation of a dam or reservoir, etc. These are the "true" DPOs.
2. Those which were renamed (like "burgh's" losing the final "h" in the 1890s), conversion to a branch or station, name changes (Hot Springs, NM to Truth-Or-Consequences, NM in 1951), etc. These population centers did not wither away. Chestnut Hill is such a case. From Postal Bulletin #6554, dated August 28, 1901, which shows the change of status of Chestnut Hill from an independent PO to a station of Boston:

Note the use of the word "discontinued" and NOT the word "dead".
Naturally, the value of any item is driven by typical supply/demand, but I try to keep the difference above in mind between an office which petered-out in X years as generally being much scarcer than an office which name-changed after the same amount of time. An 1890's postmark from Chestnut Hill should not be scarce. Just my 2 cents, your mileage may vary.
Add: the Chestnut Hill postmark just closed at $81 (plus tax and shipping) with a 4-person bidding war, despite an $8 price penciled on the reverse side at some time in the past. $8 seems about right to me.