If going withe the Fat Boy,
I believe 99-06 will work, seeing how the FLSTF rear fender went to 200 mm rear tire coverage in model year 2007.
If going aftermarket instead of MoCo, I would check with Jireh Cycles for bodywork...good products at a reasonable price with excellent customer service.
'06 Softail Night Train
Stress In / Solace Out