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I have this 87 Heritage and whoever set this up, has run the fuel line from the petcock to the carb, with a filter in the line, but the line they have is sitting between the cylinders on top of the block kinda wedged inbetween the bottom of the jugs encased in a wire harness cover (like you would see on a car covering a wire harness. I was running the other day, outdoor temp was upper 80's and right before I got home it started to act like it was running out of fuel. I quickly switched to reserve but it continued to act like it was starving for fuel. If I would run it real easy it would stay running, but if I tried to give it RPM's, it would act like it was starving again. I went home and pulled the plugs after it cooled and they looked normal. I had a new set and stuck them in and waited until the next day to test it. Seemed to run normal to the gas station 3 blocks away. and filled up and seemed to run normal on way back. So the looming question is does anyone else tuck their gas line between the bottom of the cylinders? I know this isn't right and will correct it.
I have Never been able to run an inline filter without Serious Problems...and, It is absolutely unnecessary..Ensure a Clean petcock strainer, and Ride On!!! Or...
^^^^^^^ Loose the inline filter and make sure your petcock filter screen is clean as stated by Racepres.
Line should be routed between the cylinder heads to the carb without the line going down and back up again, this will always cause issues. Line should be from the petcock to the carb so the fuel flows downward all the way to the carb
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Fuel vaporization possible?
^^^^^^^ 
Loose the inline filter and make sure your petcock filter screen is clean as stated by Racepres.
