It's all about one word - Garmin!!! The 196 will probably be my next choice. Have used the 295 quite a bit. Own a Pilot III and an eTrek. You want something good in the $100 range, the eTrek is the answer IMO. Some will say Magellan 315(?) maybe. You can get airport info off the web and dump into these. Can also do it with the eTrek I've heard, but I've never seen it done.
I use my eTrek as a backup or to follow along on cross countries with students. Get the lat/long out of the AFD and punch in the airports for your trip. The eTrek has some other features I like. Very small (size of a pack of cigs), very easy on batteries, acquires signal very readily and just as accurate as the $1000 handhelds.
This is my recommendation based on your price requirements. You have $4-500, get something with airspace overlays. See my first comment at the top.