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You could take the stock fender and fit it so you can weld it to the swing arm. Dont know how to explain how i mea, but imagine looking at the bike from the left side, with the rear fender in stock position.. Now you grab it and start turn it countwr clockwise untill it hit the swingarm.. Cut it so it is straight at the swing arm and weld it on... Offcourse it will get alot shorter this way.
Do a search for "swingarm mounted fender build" There have been a few who have done it, the biggest thread is from Robbie13. It will give you a good idea of whats need to get that fender mounted up the way you want it. Good reading too!
I did a 200 tire conversion on my 2004. I don't think you can get away with a 200 on a 1999. The swing are is to narrow. HD used a wider swingarm starting in 2000. The 2000 swingarm might fit your bike. You will need to check with your dealer. The P/N for the 2000 swingarm is 47820-00A.
I made a video step by step collection of my project. I have it on You Tube.
Go to You Tube, in search type, bikerjoe2. It will bring you to my videos.
I cut the struts off too. I used Rocket Bob's Voo Doo fender.
I can't address the fender, but you can definitely run a wider tire by converting to a chain drive. It will take a bit of research though. Without the fender as a limiting factor, your real restriction will be the space between the arms of the swing arm. I have a 2009 Street Bob that has a 17" 170 tire on it running a 1 1/8" wide belt. The space between the arms is about 11" (as close as I could measure with the wheel in place). With a chain, I could probably run a 180.
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