WOW, " Not paying more $5 k"................ that is sad that you do not place more value in these than that. We whom own them and have invested in them money and time would not part with a good dependable Gilroy Chief for that. With all the upgrades (starters, ignition systems, 6 DDT, and such) 5K is a give away. Personally if you offered me 5K for my 99 Chief you would see a look of shock on my face, then a look if insult! At this time I would say that most owners of 1999-2000 Chief owners out right own the bike and have no need to sell it so your offer for a dependable rider at 5K is not enough to even make most of us (hope that I am not speaking out of turn here) take you serious. Now for 5K I do have a complete set of 1999 tins totally ready for paint that I might let go, you could buy a cheap "everyone has one" Harley and be able to create you a clone bike.
My 1999 is slicker than it was new in 1999, all the Indian factory add on parts that I could get as well as a 6 speed DDT so not meaning to sound rude but again I would say on this forum 1999 - 2000 Chief owners wont even take this serious. My 1999 Indian Chief is priceless to me, I own 5 Indians all together and that 1999 has more value to me than any of them. At this point the 1999 Chief owners are hard core owners who have no desire to sell................. and I am sure that you have looked around and that is why you are here making an offer, no one truly wants to sell them!
Like they say, "if you got to ask how much then you afford it". Just come prepared to pay at least 5X your offer and we may have a point to start at!....... but I would have to say I doubt it.