SRQSEEG,
I am sorry to hear your disappointed. If this were my bike and someone did 109 dyno runs on my tires I would be asking them to replace the damn tire. That is a lot of wear you just lost and paid for on top of the cost of the dyno tuning. Is there much tread left I would check this for safety sake ? I sure hope the tire was at 40 psi and not higher to inflate your numbers to justify someones inability to tune the bike.
Some things to consider were your rpm's, 4th gear would probably have been the better choice especially since you were somewhere around 2000 rpms to start and at 60 around 2400 to 2500 rpm. the downshift would not have beat you up and it would have made the motor run better. Look at your dyno runs your power isnt really starting until then anyhow. 3500 rpm= about 70 hp.
Beyond that you have to realize you have a stroker motor with an EPA cam in the bike not a bad cam not a great cam for low end torque either. Trying to roll on in 5th gear on a 9% grade from 2000 rpm's or 2500 rpm's would be tough considering the pull up hill and your in a cruising gear not a real pulling gear. I think your expectations are a bit unfair for the test you gave.
You may want to consider some other choices like a 251 cam pulls a bit more than the 253 or another brand of cams. S&S 570, Andrews 55g's Woods tw6gh.
While these are options available to you I must ask why you wouldnt have downshifted built up the speed a bit as well as the rpm's and then tried 5th gear which is normally used as a highway gear / cruising gear ie 1:1 ratio
Things to recommend which haven't really changed over time
Mapping Tuning
For Torque down low a 2 into 1 pipe
SE Air Filter / Ness Big Sucker / Zippers /
Cam's Harley chain drive or GEAR Drive
Head work
Gearing changes / and or a 6 speed to offset this for highway
As examples 24 tooth or 21 tooth front counter sprocket, 37 tooth clutch basket, 29 tooth front belt pulley etc etc
Larger Throttle Body
Gotta pay to play

If I can help with anything let me know.