I do almost all my planning off the map (chart)
then goto the waypoints nearest where I actually want to go via.
(aviation in my case being almost exclusively a method of getting from point A to point A)
I would encourage you to have more than 1 gps on the go, in my limited, sheltered, life it's not unknown for the beasties to keel over (almost always power related issues, but never easy to fix in the air) best to have some redundancy built in.
Given that a lot of my flying is spent significantly above clouds, Maps are all but useless anyway.
modern gps software makes airspace avoidance simple as it works in 3 dimensions, you can have vertical separation warnings and horizontal separation warnings, show or hide various pieces of airspace to your hearts content and have warnings for whatever you want, at whatever distance you want.
each to their own.
I have the utmost respect for those who choose to use a map, but I know I can't fight with a map and fly at the same time.
cheapest way to do it?
get a smartphone with all the bells and whisltles on a cheap contract (Winmo)
install Winpilot VFR.
that'll cost you less than a dedicated GPS and give you a phenomenal piece of kit, showing all airport info, frequencies, airspace, yada yada yada, for what you would be paying for yer phone anyway + the cost of the software. (with limited battery life, watch that)
on a half decent contract you can have free 'tinternet on it and it'll show realtime weather too. (separate programme)
takes a lot less to understand the modern software than it does to understand VOR . . . . and it's faster / more accurate / less fiddly / less operator dependant / i.e. safer.