Two questions on VFR flight following into an uncontrolled field

Appreciate this groups insight ...

When getting VFR advisories into an uncontrolled field, when and how ought
one transition to the CTAF. Currently, I tune in and monitor the CTAF on
COM2, and if ATC doesn't tell me "squawk VFR, freq change approved" by about
5 miles out, i get antsy and cancel advisories. The theory is that I really
want to be focused on other traffic on the CTAF, and the advisories aren't
always that helpful "numerous targets in the pattern...". Also, there is
sometimes a lot of chatter on the ATC frequency, making it easy to miss a
CTAF transmission even when monitoring it. Should I just cancel advisories
proactively 10 miles or so out so that Ican focus totally on the CTAF? Or
should i really let ATC take the first step, with the assumption that they
know best their abilitiy to provide quality advisories, and they'll drop me
over to the CTAF at the most optimal time. I'd be interested in the
different opinions on this... What if i only had one COMM (like the C152 I
on occassion fly).

Second question. Check out http://skyvector.com/#29-15-3-2383-2408, i was
flying into MGJ (Orange County) at 6500 from the E, getting advisories from
NY Approach. Actually the flight from the Ebrought me right over the SWF
(Stewart) Class D airspace, which has a 3000 ceiling. So I was in my VFR
descent actually right over Stewart, being careful and then some not to bust
the 3000 ceiling until i was well clear of the Class D, which gave me all of
2 miles to get from about 3500 to the 1400 TPA at Orange County. Rwy 3 was
active at Orange County, so i overflew the field, went about 1-2 miles to
the West, descended aggressively and entered the left downind on a 45, still
descending 1200 FPM right up to the downwind turn. Somewhere right over the
field, NY cancelled and i turned over to the CTAF.

OK, on reflection this did not strike me as the safest way to do things.
For one, the aggressive descent just outside of the downwind, in a field
that has a fair amount of turbine traffic flying (wider and higher) patterns
right where i was descending through. For another, i would have rather been
at TPA a fair bit out, so that i could have the benefit of monitoring the
pattern at eye level. Ideas on how to do this better? Some thoughts that
come to mind a

* Be more patient, go to the west even more, say 4-5 miles, give it time for
a gentler descent, and enter on the 45 at the TPA.
* Be more patient, and navigate to the N or S to avoid Stewart's Class D
altogether.
* Could I ask NY approach to talk to Stewart tower and see if i can get
permission to descend through Stewart's Class D. Might they do it and would
that be legal anyways -- or would i have to talk directly to Stewart tower?
* Or would i just ask to cancel flight following in the vicinity of Stewart,
talk to their tower, tell them the deal and ask to descend through their
Class D enroute to MGJ?

There's large turbine traffic low all over the place here...

Any other ideas?

Thanks all! Tman...