Someone should really write a guide for doing that, i'd love to play heavily modded skyrim but its so intimidating to sort through all the mods and figure out which ones are the best/aren't broken/etc.
Its been ages since i've played it and i've been thinking about playing through it again.
BOSS takes care of a lot of it. The rest is down to reading the notes on the mods' pages.
I use the top 100 all time list to get the general enhancements and QoL improvement mods.