I am of the opinion that if a neck heel needs to be pushed hard into the pocket, it's too tight. If the fit is that tight, it will cause other problems later on, both during the build and after it's finished. The neck heel should almost literally "drop in" to the pocket with little to no resistance.If the neck pocket was a tight fit before finishing, then it's easy to overdo it and have the neck then too big to fit in the pocket.
If I have an unfinished body that has a tight pocket, I sand it until I get the fit "right" before I do anything. Especially before applying any finish. I want to create enough space to accommodate that and more.
If it's too tight, it can make proper neck/string alignment hard to achieve AND if it's too tight the risk of cracking the finish around the pocket (especially the little bit nearest the lower cut-away on a strat) is increased by neck movement either by adjustment or natural environmental conditions (shrinking/expanding with humidity levels).
The myth which has been perpetuated about a tighter neck pocket creating better "sonic transference" and "more sustain" is rubbish.
I will clarify that I am ONLY talking about bolt-on necks here.
I'm not saying that the best possible mating of the surfaces of each component shouldn't be considered, but it is not the be all and end all to a great sounding electric guitar. How many great sounding vintage strats & teles have had an old business card jammed under the heel as a shim?
I don't find this to be difficult at all. I have small hardwood blocks that are cut true and square just for this purpose.Whilst it's easy to sand the finish on the heel of the neck flat, it's a lot harder to do a similar thing within the confines on the neck pocket.
By using the sides of the pocket as a guide, I can sand the bottom perfectly perpendicular to the side, and vice versa sanding the sides using the bottom to maintain a right angle to the side. I take my time and check regularly with a machinist square.
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