Thanks for the replies everyone.
To answer a few of the questions that came up.
I would be painting it for my own use as I plan to keep the LT. I absolutely adore the bike and how it rides on long trips and while I enjoy some of the newer 2008 - 2009 features, having done all the major work on my '99 including the clutch, I know it's faults and quirks well. I know the bike itself is only work $2K - 3K at most even with nice paint and fresh parts and I've already got more than that in repairs, parts and upgrades.
I have the supplies to do the work as I do small painting work & stain on wood with a small sprayer and an air compressor. I called around for a few quotes and while most shops said they wouldn't even touch it, the two I did find were over $2,500 and that's if I bring them the panels off the bike.. so this is something I would be doing myself. As mentioned, i have thought about picking up some extra tupperware parts to "practice / test" my hand on spraying and checking the color consistency before moving on to the nicer ones already on the bike. It would also be a good opportunity to replace some of the chrome that has come off over the years and brighten the bike back up.
I'll probably take this on in the spring / summer time so have some help from the weather with temperature.
It sounds like you judge worth like I do, which is different than most. Most people assess value based on what they could sell the bike for. That is certainly one valid value metric. I look at value as what it would cost to replace what I have. I kept my 94 Chevy truck and snow plow for 20 years. For the last 10 years or so, I put about $1,000 each year in repairs. This for a truck that was “worth” probably less than $5,000 for the last 5 years I owned it. My wife often thought I was nuts to keep putting so much money into it each year. However, my rationale was that to replace that truck and plow would have cost me at least $600/month in truck payment. So, every two months I paid for my annual repairs to it. And it remained reliable and got the job done so I had no reason to sell it.
I am not one who has this need for something new all the time. I have more than happy to keep a vehicle a long time if it remains reliable and gets the job done. I keep my LT, not because I can’t afford a new bike, I easily can, but because I have yet to find a bike that fits my mission profile better than the LT. And I have tried all of the available options from Harleys, to Yamaha Venture Transcontinental, to Gold Wing, to K1600 GTL, GA and R1200RT. None do long distance two-up touring better than the LT. They all do various things better, but for the way my wife and I travel, the LT remains the best fit. So, I am putting another $2,000 or so into this year in preparation to ride to Alaska, even though the LT itself is “worth” less than $5,000 to a dealer on a trade and probably less than $6,000 in a private sale.
Many consider such spending to be wasted money, but the closest bike we have test ridden that could replace the LT is the GA, and that would cost me $27,000 for a bike that overall isn’t any better than the LT for our mission. Yes, the GA is more powerful, handles better (although less stable behind a semi), brakes better, is lighter and has more electronic gizmos, but it is less comfortable and provides poorer wind protection, particularly for my wife. So, for me the value equation is spend $2,000 for another year or two on the LT or $27,000 for a bike that we really don’t like any better than the LT. For me, that was a fairly easy decision even given the maintenance headaches that come with the LT. While cruising down the California coast, or across Death Valley, I wasn’t thinking about bleeding the ABS, but just enjoying the ride.