We both like our 'creature comforts' and don't think that either Rey or myself could spend time on a boat that is akin to camping out.
When we bought the big Gulfstar it had never been set up for long term cruising. When we added cruising systems, simplicity and ease was foremost in our minds. We have only one electric winch on Tropical Dance. That one electric winch perform multiple tasks (raises the main, furls the headsail, hoists me up the mast, adjusts the main sheet and puts in the first reef. If it breaks, we don't need it. We just go manually as we did for the first 4 years of cruising on the boat. Our main is standard 'slab reefing' with 'lazy jacks' and the headsail can be furled 30% and still keep a reasonable shape ( of course reasonable is a relative term ). All the pumps can be interchanged so if one goes out we swap it for another or a backup that we have. We even decided not to add a watermaker. Don't need the headache and we carry 350 gallons. Our 2 refrigeration systems are one piece units that are drop in and plug. I think that the only truly complicated system on the boat are the air conditioners (two of them).
The two pieces of equipment that I don't want to break without the ability to repair are the auxiliary engine and the windless. The thought of wrangling our 88 lb Delta manually isn't a pretty picture and the engine?,, that's a necessity we all share. No way around it.
I think that you hit the nail on the head when you typed the word 'requires'. Anyone purchasing a boat that requires the use of electric assist or has complicated sail management to make the boat sail is bound to have trouble.
Yeah, we like our creature comforts but we don't need them to make the boat work.