JMHO but as Joel and ThunderRogue prove, the cam chest is nothing to be afraid of. I am sure both ot them will tell you not only did they save some $$ but the feeling of accomplishment is even more rewarding. Some repairs on Harley's are more challenging than others but replacing tensioners, innner cam bearings, installing cams, anything in the cam chest defiinitely falls into the DIY category of projects.
Those early spring loaded cam shoes are known for early failure without warning and can cause bad juju. At 36K miles they should have been replaced with aftermarket parts, CYCO are the current "go to" replacements. Once the cam chest is open, changing the inner cam bearings is a good idea. OEM lifters should be replaces with aftermarket parts as well; Johnson Hy-Lifts from WFO Larry are the current "go to" replacements.
The indy was cutting the OEM pushrods to avoid removing rocker covers and rocker arm support plate; time saving approach and the reason for adjustable pushrods. I have changed cams, pretty much the same operation, in less than four hours so I am pretty sure the indy could match or improve on that.
The only real challenge for a DIY guy is the pressing cams in/out of the cam plate. If the indy charges $125/hour for labor, the OP could easily do everything else and pay the indy to press the cams in/out and even if the indy charged for an hour, the OP can do the job for about $600 plus the cost of the HD service manual. R/R of the inner cam bearings will require the purchase of the tool which is available for about $75 on Ebay.
If I were the OP, I would suggest taking on this project at 50K miles; it's not a difficult project for anyone with basic hand tools and mechanical skills and the HD service manual. I would not trust the spring loaded tensioners past 50K miles. I konw ther are some that have never had issues but there is a reason the MoCo replace the spring loaded setup with hydraulic tensioners and roller chains '07 up.
There are plenty of DIY YouTube instructional videos posted by DIYers; some better than others. Check out this guy replacing tensioner shoes.
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Apologies for the long winded post but I try to encourage DIY projects that are usually within the skill level of most of us.