We've been swamped at work, so I haven't had time to come here that often, plus I think this kinda flew over my head heh. And like NYCCommuter, I ride mostly prospect park. I stay off the bike paths in the park and go on the roadway, at some points in PP, the roadway is 3 lanes wide. I mean there's still morons there but not as many as there would be if I were to stay in the roadway.
Riding around the city is pretty interesting if you find a couple of friends to do it with, that way you're not restricted to the parks.

As far as winter clothing's concerned, here's what I wear:

130-180: Wuss out.
115-130: Shorts, loose white long sleeve mesh jersey, ride slower.
100-115: Shorts, loose jersey.
55-100 degrees: shorts and jersey. Skull cap.
40-55 degrees: long sleeve top, jersey, tights and shorts. Skull cap, ear warmers.
30-40 degrees: long sleeve top, fleece powerstretch jersey, tights and shorts. Skull cap, ear warmers. Full finger gloves.
25-30 degrees: long sleeve top, fleece powerstretch jersey, tights, shorts, legwarmers. Skull cap, ear warmers. Windproof gloves.
15-25 degrees: long sleeve top, fleece powerstretch jersey, tights, shorts, legwarmers, windproof vest. Balaclava. Windproof gloves.
10-15 degrees: long sleeve top, fleece powerstretch jersey, tights, amfib windproof tights, windproof vest, booties. Balaclava. 2-layer windproof fleece gloves.
0-10 degrees: fleece sweater, windproof jacket, tights, amfib windproof tights, booties. Balaclava, ear warmers. 2-layer windproof fleece gloves with liner.
-15-0 degrees: long sleeve top, fleece sweater, windproof jacket, tights, amfib windproof tights, booties. Balaclava, ski-mask/heat exchanger, goggles. Down gloves.
-45 - -15 degrees: long sleeve top, fleece sweater (down sweater near -45), windproof jacket, tights, fleece pants, windproof pants, booties (heated socks near -45). Balaclava, ski-mask/heat exchanger, ear warmers, goggles. Down gloves (with liner near -45).
Below -45 F: Wuss out.