Hello Ian, nice to hear from you.
I’m all too familiar with that stage of learning CW. I started learning CW via an app on my 'phone that uses the Koch method, called IZ2UUF. I used the app to play random letters, which I would type into a text editor on my 'phone, this allowed me to easily monitor my accuracy. I started late in February, and by early June I had completed all the letters and numbers, and was operating CW from home by typing into a text editor and reading it back. So I thought I would try an activation. I took a tr(u)sdx radio with me on a backpacking trip, along with a cheap set of plastic paddles. All went well calling CQ until I started getting calls back and realised I had absolutely no head copy, I couldn’t even write down with a pencil what was being sent. It had not occurred to me until that moment that my learning of CW had given me the very specific skill of typing out characters, and nothing else! I had to grab my phone quickly to start typing in callsigns. I spent the rest of year working on gaining head copy, and it wasn’t until around Christmas time that I was properly conversational at 20 to 25 wpm, so the full head copy transition took longer than the initial learning.
I still think that this was a good way to learn though, since it minimised the time taken to get to a point where I could hold a QSO, even if that meant typing and reading it back.
Harrogate would be a lovely place to start off with, and the antennas business is not too problematic – an end-fed half-wave, either add your own wire to a purchased transformer or buy the whole thing and a telescopic pole is all that’s required. My telescopic poles are mostly from Deacathlon, I use a compact 5m pole, or occasionally the 6m version, but Sotabeams also stock an excellent choice.
Have you got a radio in mind for activations…you’ve probably seen the excellent write-up from @M7OYL which shows that you only need a Baofeng and a whip antenna to make some good contacts. I don’t think I have ever failed to make at least one 2m FM contact from a summit.