Why do you think you looked stupid???
First of all you are a large person and with your weight it is like riding 2 up all the time as far as the bike is concerned.
You took a stock 103 and tried to out run bikes that had a 110 and a 120 that may have had performance mods as well.
If you want to out run these bikes you should just pull the 103 and put in a S&S 124" and be done with it.
If you just want a nice touring bike then a 103 with a cam, intake, exhaust upgrades along with a good EFI tuner will give you miles of trouble free smiles.
Racing proves nothing and burnouts cost $$$ money because tires are not cheap and it is hard on the drive train.
Putting a $1000 or so in your stock 103 will give you some nice power for touring/cruising and lots of cash in your pocket.
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08 FLTR candy red sunglo,with 2015 103 HO, V&H Dresser Duals with Monster Rounds, Power Vision tuner, Willy Shiny Wheels and Forks and a bunch of other stuff.