Hello Stump and welcome to a friendly forum!
Things are a bit quiet here since Covid re-arranged things regarding travel....
But I'm pretty sure that if you ask specific questions you'll get good answers.
When you say "newbie" - do you mean newbie to the forum or newbie with regards to Italy?
And if you do have experience in Italy, you might want to relate a bit...
Newbie to the forum. My wife lived in Roma some years ago & I have walked some of the Via Francigena. We are looking around Umbria (digitally, not in person) at various cities/villages for ideas. When we can finally do the research with feet on the ground, we hope to have a shorter list of possibilities. Spoleto is on our list, as is Umbertide. Hopefully as we watch the forum, we can pick-up information & ideas.
Our one foray into Umbria several years ago had a humorous aspect which your post reminded me of. We were to have dinner at a recommended place and got somewhat lost. I kept asking directions for Umber Tide and no one had a clue what I was talking about. That is, until my wife overheard me (she had been driving and not paying attention to my verbalization) & started laughing, correcting my pronunciation to the Italian um-bert-te-de. We found it easily after that.
As a side note, the Rome based restaurant reviewer/tour guide/blogger Elizabeth Minchilli has a free app. called "Eat Italy" and I believe that the Umbria specific section within it is free as well. (https://www.elizabethminchilli.com/apps-rome-venice-florence/). She has a 2nd home in Todi and has written a lot about it and the surrounding area, so its pretty accurate.
Hi there. I can offer some advice through my articles for International Living. There are plenty on their website that are free, so be sure to check those out. There are so many choices; it all comes down to the atmosphere, size of town, amenities and lifestyle you want to have.