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Sounds like it could need a lot of work. I would offer less than he's asking...
went and checked it out today. seems to be in good running order but has been stored outside for the last 11 years. faded paint rusted bolts and two dents in the tank. not to mention he droped it twice and broke all four turn signals. i think it just needs a little more work cosmetically then i have time for.
Not a bad price depending on the add-ons. I also have a 99 1500 for sale.
First thing I'd do is take it up to 60 and be in 5th gear. Then crank the throttle and see if the clutch slips. I had this problem and there's lots of information in this site if you search for 'clutch.' The problem is easily fixable for a reasonable amount but it is the major flaw of the 1999 year 1500; I have one and had very good luck with the repair methods herein.
Otherwise, mine's for sale for $2900 and I think that is a good price if it's running perfectly and has new tires and battery.
Varooom
Fantastic deal... so long as it has been maintained.
I gave $4800 for my 2001 with 15,000. The only add ons the bike had were V&H pipes,
hypercharger (big mistake!) and Tach.
there is a 99 drifter 1500 for sale in my area for $3000. it has a little over 16,000 miles and he says its in good condition. just wondering if this was a good deal. 
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