The idea of a guesthouse sounds good; I have no experience with this, however, and wonder about any associated costs ?
"However, I am more concerned with how I would handle my actual travel gear (electronics, clothing, maps, books, etc.)."
I really like the idea of multi-use stuff where all of that is carried on the trip, and hopefully this doesn't weigh you down too much. That depends a lot, of course, on the type of trip under contemplation. For my one experience, having a hut or youth hostel or B&B to sleep in every night certainly limited how much "backpacking" gear needed to be carried.
But electronics for me can be just a smartphone, plus optionally a folding bluetooth keyboard. Clothing is much like a long distance backpacking trip --- a couple extra pairs of underwear and liner socks, wash these in the sink at night. Books --- on my smartphone in eBook format. Maps: well, these get lighter as you go at least, and for the type of trip my wife and I did, we were fine with sharing map/guidebook pages. Really, most of what we had with us was used most of the time.
We did buy a new backpack for the trip, one of those somewhat bullet-proof but heavier "travel packs" where the shoulder straps fold under a zip-over flap and you can check the thing like a suitcase with some hope of not having it destroyed by the airline baggage handlers. This was our checked bag and served as my backpack, with a somewhat smaller backpack for my wife to use and act as our shared carry-on bag on flights. Worked out well for us.