I had a 99 Tinkie road king classic with mm fuel injection. Loved that bike...I never "needed" more power until i rented a 2013 road king....
I looked at the options of big bore kits, cams, etc and decided to trade mine in for a new bike. i am not afraid of performing the work or even afraid of reliability, but in my case, i got the new frame, updated fi, etc.
In your case, you got a good base to start from. No replacement for displacement so the big bore kit would be beneficial along with cams, etc and you can still run 91-93 octane...or you can get high comp pistons and run higher octane fuel...

 

I hear you on wanting more power, my 95" cvo was fine till I test rode my sons 09 Electra glide with a S&S 106 kit. my engine build started a few months later.

 

Find a good independent Harley mechanic that you trust, tell him what you're looking for and your budget, deliver the bike, and stand back. Simple as that. Most of them have a 'recipe' for what you're looking for, know what works and what doesn't work. Write the check. Ride.

 

go for a new bike.....2014 will probably do.

 

Depends on what you want more power for.If you're looking for more fun then yes cams head work big bore etc.If you're having a problem pulling hills fully loaded with a passenger then look at gearing.

 

I have an 2010 Ultra with 96 that had Stage one with as PC-5. Upgraded to Power Duals and SE255 with a good dynotune and gained 36% more HP & 35% more torque and am happy as can be. I lost no reliability. I'm sure there are much faster and better pulling options out there, but for the $ I spent I am very happy. It's a touring bike, not a canyon racer!

 

Completely depends on how fast you are racing to.

 

Depending on how extreme you want to go, Instead of wasting your time with cam upgrades, head work, etc. I would just procharge it. For roughly $6k you will double your hp on a stock engine. That's what I did when i first bought my bike. I ended up with 121hp and 108 ft-lbs of torque (everything else in the engine was stock).

 

.....he will explain the various things that can be done, plus the benefits of each stage of upgrade. Be aware that if you decide on a small improvement you may well find you would like yet more, etc. In my case I am at my third stage of 'improvements', with over 100/100 and can see the case for yet more! 130/130 may be a bit too much, but how do we know until we get there?!

 

Tuner + tune, cams, big bore, headwork, sportbike. How fast ya want ta go? Set a power and/or budget goal and talk to a few builders about it. Pick the one ya like. There are too many good choices out there for us to pick one for ya without a lot more info, as each of us has a different idea what " more power" means.