It' my guess that, just like when you buy a car, when you walk out the shop with your newly purchased production guitar, its monetary or resale value will drop... because now it is "used." Don't know if the same is true of boutique guitars or those custom made by independent luthiers.
One way to get around this is to buy used... I purchased a '92 D-55 off eBay for ~$1100, very playable with a few cosmetic issues, but my ear doesn't see those. Unless I mis-treat it in some way, I don't expect that the value of my D-55 will drop much thru the years. .. it may even begin to appreciate at some point. I may have to put some maintenance $$$ into it at some point... but that's true of any guitar. Of course, there is some risk to buying a used guitar sight-unseen (so far, I have come out OK on 4 of 5 eBay purchases, and was able to return the one "dud" for a full refund)... and LTGers are usually happy to help you "check out" a guitar for sale in the neighborhoods.
D-55s have been made in Westerly, RI; Corona, CA; and Tacoma, WA. I don't know if any were made in Hoboken, NJ. Some view the Westerly era as the peak in Guild quality (other die-hards swear by Hoboken or NewYork made Guilds)... But Tacoma-made Guilds have gotten excellent reviews from die-hard Guild fans... with the current move in progress interrupting production, Tacoma-made Guilds may be in demand (and prices may rise). Production in Corona is viewed as suffering from some quality-control issues... but among the problems some excellent guitars were made that can still be found at bargain prices.
On the other hand... I don't think many of us at LTG focus much on re-sale value nor buy with the idea of guitars as an investment. We buy for aesthetics... tone, appearance, history, feel, "soul"... or other intangibles. If I found the guitar of my dreams, I'm not sure I'd worry to much about it's re-sale value... because I'd never sell it.
Dave