Sorry I didn't see the new post here.
I would say "Neither of the above" to your two current GPS units of interest.
I don't like touch screens to begin with, but if you're thinking to go that route, I would look at the new Garmin Montana.
The Delorme is a good GPS - in function, they're all pretty much the same.
The reality is, like it or not, Garmin owns the recreational GPS world. There are more aftermarket maps, products, etc. If you don't care about that (but you probably will end up caring) then go with the Delorme if you like that.
I use a Garmin Rino 530HCX on my WR usually. The other choice is a Trimble, and you don't even want to know what they cost. It rarely offers any advantages over the Garmin.
Also on the bars with the Rino is a SPOT. I don't really want a SPOT hooked up to my GPS so that if the GPS gets toasted, the SPOT does as well. And the SPOT standalones are so small that a combined unit doesn't add much in my opinion.
Garmin, Delorme etc all get their maps from the same sources i.e. in Canada, they get their mapsheets from Natural Resources Canada. In the US, from the USGS. So they can theme them differently, but they all have the same base data. When it comes to choices in maps, Garmin is head and shoulders above everyone else. Try and find something like Backroads Mapbooks, made for Canada, in a format other than Garmin. Or Dale Atkins' Ibycus project of topo mapping for Canada and the US. Guys write software for the largest potential market, and that's Garmin.
Some Garmin maps are coded to the one device; some aren't. It's their attempt to deal with piracy. Other Garmin options are purchasing the maps on a SD Card. Then the maps are on whatever computer you stick the chip in - but it can't be on two at once. I have multiple Garmin mapsets and do some development work for another GPS map company; I don't see the licensing as a problem for the use that is intended.
Your GPS doesn't care what operating system you hook it up to. What it does care is if the manufacturers proprietary software is on that computer. Much of the GPS-related software is Windows only, so you can fight the tide or go with a Windows emulator - this is one of those Mac advantages.
For your phone, the leader of the pack at the moment is the latest Android devices. Craftycoder over on ADV has written a nice little utility that allows an Android to cache maps beforehand, so your Android phone can still serve as your GPS, even when you are out of connectivity.
This GPS has just been discontinued, simply to bring in an advanced version with more useless bells and whistles, but this one would be my first choice:
http://www.amazon.com/Garmin-GPSMAP-60CSx-Handheld-Navigator/dp/B000CSOXTO
Or this one (which I use), also discontinued in favour of a newer version which I like less:
http://www.amazon.com/Garmin-Rino-530HCx-2-Way-Radio/dp/B000QJNC78/ref=sr_1_1?s=electronics&ie=UTF8&qid=1312354062&sr=1-1