My opinion: people will wait until you get desperate to sell, and hope that your need for cash makes you sell 'upside-down' on your price & work put-into it. These bikes are probably close-to being bottomed-out in value, though I think they can go further-down in value. What will REALLY kill the VMax Gen 1 is if Yamaha stops supporting them. Some parts are already unavailable except NOS in someone's inventory, or from used bikes.
My opinion, the two VMaxes having value above just being a used old bike are the first year and the 20th anniversary. The less altered, the better. From dealers, the prices would be better (for them, i.e., higher sales price), because they usually offer some type of warranty, even if it's only a month. Private sales are usually less $ exchanging hands, because it's "as-is, where-is," no warranty.
Spending $2,000 at a shop to get your bike in tip-top shape is probably a waste of money that you will never recoup. Every used bike is going to have things which are NOT "as it left the factory," whether it's oxidation on the clear-coated die-cast aluminum pieces, or the black painted pieces, specifically the engine. The fenders and faux gas tank cover can fade, especially for bright colors like reds. Upholstery rips, seams split, forks get pitting: OEM fork seals and aftermarket downtubes will run you about $450 for the parts, and then installation costs, if you cannot do it.
My opinion is that you do what's necessary to get the bike safely operating, reliably, and don't try to make it "showroom new," because the market for these just isn't there to be purchased at a high sale price.
The market for clean later-model VMax bikes is probably more-in the $3,000-4,500 range from what I've seen. There is a continuous supply of them here, where we ride 12 months of the year, and have a resident population of 6 million in the tri-county area (W. Palm Beach, Ft. Lauderdale, Miami). You see some people asking the bucks, but those bikes stay on CL, and over-time their prices eventually come-down, before they are gone.
The disadvantage is that if you can't work on your bike yourself, you have to pay $$$ to have it done, and the number of shops who will work on them is small. I've heard of dealerships refusing to work on them, because of so-many things being wrong, and they don't want to risk the customer becoming an "eva-since" customer: "eva-since you put on new tires and brake pads, my bike's been idling crappy, and the battery's dead!" One has nothing to do with the other, but try explaining that to a no-mechanical-aptitude owner, who then turns to social media to sling mud at the dealer.
Hopefully you will find someone who wants a first-year bike, and who sees the quality of care it was given to avoid problems in the carburetion, charging, and 2nd gear wear these bikes are prone-to developing with the passage of time, and use.
