I'm going to regret wading into this, but here I go anyway....
I've been instructing EMCOMM teams on WE for quite some time now. It can be rather challenging to say the least. While the folks in this group are not likely to struggle at all with an RPi or Linux or even UNIX, and can probably compile a kernel blindfolded with one hand tied behind your back, you are not the average EMCOMM operator. Most of the EMCOMM teams I train struggle with zipped files! They really don't want to use anything that ends in X (except maybe a few OSX people).
Do I like WE? Not really, but it does the job. Would I rather have something more robust that runs on Win, Linux, Unix, OSX, iOS and Android? Absolutely, but it's not going to happen. I can't even tell you how many people who have told me they were going to write something waaay better. It either never happens, or gets only as far as early and ugly beta with no documentation or support. Meanwhile WE plugs along, gets a little better with each revision, and is in continuous support and development. So you need a Windows box, get over it. My portable station is a Win10 Tablet with keyboard that cost me less than $80. It runs WE and Direwolf just fine, and it would happily connect to a DRAW for RF connectivity if one was in WiFi range (or it can use a number of other hardware options).
If you are going to write something waaay better, let me know when it is done, I'll beta test it.
Until then, we're getting by just fine with WE.