Well, I think that I'm an expert (or at least a legend in my mind).
I CAN tell you that a used guitar will fetch about half of it's street new value (the actual tagged sell price at a Guitar Center for example) IF it's in really good condition.
(One does know that ALL THINGS therein are negotiable?)
Guitars have poor resale value. Putting expensive replacements into a guitar has little effect on increasing it's resale value.
Money well spent, is just, well, spent in this case. Bass guitars fetch even less.
I often buy the really deep discount guitars at Guitar Center sales and just resell them or trade/sell to a music store (never the GC since THEY KNOW what you really spent on it there.
I've bought a Squier P-Bass Special new for $50 and resold it for $125 (hmmm, about it's trade-in value).
I got an Ibanez piezo/humbucker guitar (?something420?) for $300 and resold it for more (hmmm, about it's trade-in value).
An EMG DG-20 pickup/active tone module loaded pickguard which will cost about $250 street will fetch maybe $75 to $100 in trade-in and not much more in resale. Most Duncan American pickups go used for $40 to $50 (and they anticipate that you will negotiate $5 to $10 off of that). That means that they are willing to pay about $15 to $20 for them.
Putting good pickups into a relative good guitar (to me this means a $500 to $1,500 guitar) will increase its value a little. It will still be a $500 to $1,500 guitar.
Putting good pickups into a cheap guitar will increase its value very little. It will still be a cheap guitar.
At this time, I'm considering a new Am Std Strat HSS in Sienna burst ash body rosewood board at a local store. Street price is $1,080 (list is $1,542). I can get this guitar for $750.
Now, before anyone gets excited, it's resale value the next minute will be about $550 to $600, maybe. So, I look at this as "am I willing to burn $250 for the pleasure of having this guitar for a while." Well, yeah, maybe twice as willing as if I were "losing" $500 at street price.
This gets me into nebulous territory in that a good aftermarket build runs about $1,000 give or take. While I get exactly what I want in the aftermarket build, its trade-in value is less than a Fender or Gibson of equal street price since most don't know or appreciate the value of better tone woods and finishes.
And, before one starts worrying about messing with the "future vintage value" of today's new instruments, what are the chances that there's another "slug of boomers" coming along that will be interested in the "toys of our generation"?