Try The Time Traveller's Guide to Medieval England: A Handbook for Visitors to the Fourteenth century. It's a good book, got good reviews and isn't to in-depth so remains a fun light read.
https://www.amazon.co.uk/dp/1845950992/ref=cm_sw_r_cp_apa_K6vWBbDP2QMX7
I know they sell them at the Tower of London, but I’d imagine they’re priced up for tourists. I got one there of pretty good good quality, but if you’d rather buy online they’re pretty cheap on amazon
In that case <em>The True Chronicles of Jean le Bel, 1290 - 1360</em> and <em>The Chronicle of Geoffrey le Baker</em> are both great, accessible reads. They do only cover the Edwardian War (1337 - 1360), and after that period it's hard to pick one or two primary sources for an overview.
I think it might be better to approach this as an emotional rather than purely intellectual decision. Continued excitement is what's really going to keep you going in your studies.
One way to go about would be to read first hand sources and see what grabs you more. Pick up <em>Chronicles of the Crusades</em> and for the Hundred Years War, <em>The True Chronicles of Jean le Bel</em>. Reading both you'll get a good look at the type of works and scholarship you can look forward to the next few years. That should be informative.
And of course, just because you focus on one now doesn't mean you can revisit the other in the future.
I thought the helmet looked familiar, and I think it’s the helmet on the cover of this book! I haven’t read it, but it’s probably pretty informative: https://www.amazon.com/Arms-Armour-Elizabethan-Court-Richardson/dp/0948092734/ref=mp_s_a_1_1?crid=RUP0ELT5G21I&keywords=elizabethan+armor&qid=1654058320&rnid=2941120011&s=books&sprefix=elizabethan+armor%2Caps%2C170&sr=1-1
No that is from Mankind, which came a little later. I believe this documentary was from 2005 or 2006, somewhere around there. Of course, like many programs and pop documentaries it only offers an overview, but it is well done and really inspired me to dig deeper and buy books, which is real the real digging starts. I can’t find this specific documentary on YouTube but it is available on HistoryVault. Here’s an Amazon link so you can see which one I was referring to:
The Dark Ages (The History Channel) https://www.amazon.com/dp/B000NO2416/ref=cm_sw_r_cp_api_glt_fabc_AGZPMNMWHXZ7H3RS2HSH
I agree about the tendency to romanticize the past, which of course virtually fictionalizes it, but nonetheless I think it’s something we tend to do when looking at the past in general, whether it’s medieval Europe, the Roman Empire, Ancient Egypt or pre-Colombian America. It can be a good thing though, as I’ve found well-researched historical fiction to really get the imagination going.
In the Series Jamestown, one of the characters loses her husband early on in the series and is publicly shamed for choosing to "live as a widow."
I don't know the answers to your specific questions, but I found Ian Mortimer's "The Time Traveler's Guide to Medieval England" to be an enjoyable read which addresses the lives of ordinary people. Check it out: https://www.amazon.com/Time-Travelers-Guide-Medieval-England/dp/1439112908
It's not going to have a great deal to say about Wales and Scotland, though.
Priests may have traveled to study at a university and to take their positions assigned by the Church, but that's really more about the destination than the journey.
Can't remember where I read it, but it's likely that many medieval pilgrims were really more interested in travel than any holy duties. If you want interesting accounts of travel, that's where I'd look.
You'll have trouble finding translations of primary sources. But I saw Everyday Life of Medieval Travellers in a bibliography, and Travel in the Middle Ages looks interesting.