Here is the deal. I have a 99 roadking with 50k on it. I did the conversion from efi to S&S carb set up, V&H true duals, S&S adjustable pushrods, otherwise it is pretty much stock. I have had this bike for 5 years and have been pretty happy with it. Last December I bought a roadstar for a cheap hot rod bike to play with. this thing has so much more power than my TC88 that now the HD is not as fun to ride anymore. I'm not looking for a drag bike just want some more power.
I was thinking about doing the 95 upgrade, the kit is about $750 (not bad) but then I would imagine that I would also need to add new gear driven cams, and heads. this would put me at about $2200 if I do the work myself.
So now i'm starting to wonder if it is worth it to dump another $2200 into this bike or if maybe it is time to start looking for a deal on a 2006-up bike.
Guess i'm just looking for opinions or ideas of a better way to get some power out of this bike without going broke/broker. say about a $2000 limit

 

I would rent a '14 of your choice, ride it for a day, and factor that into your decision. You know how the pre-09's ride, already.

That said, the '14s have good power stock, and handle well.

I was faced with a choice similar to yours (I had an 04 RK). I was looking at upgrading to the tune of $4-5K. Instead, I elected to buy a '14 SG. I got all my 'upgrades', and some things that just weren't practically-speaking available, e.g., the updated frame.

Alan

 

What Alan said. You never know until you get on one. And you won't recoup the money you spent on your current bike and I hate that. Plus, the longer you have your bike, the less you're going to get for it.

 

I was in a similar situation a few months back - ended up with a almost new (2012) bike...
I had a 97 Road King (evo motor with the mm injection) @ 40k miles. Mine was not as clean looking as yours. Was considering adding a fairing, thought about the 6 speed trans, needed some new chrome, convert to carb or go aftermarket fi conversion, upgrade suspension, etc, etc, etc.....

I had the bike since 99 so was pretty attached to it, BUT was gonna spend a lot of money and time to upgrade it, plus would still have the old style running gear with a lot of miles and time on them.

I went in to the dealership with the idea of seeing what kind of deal I could get on a 13 Ultra - with the 14's out, figured what do I have to lose? Handling, braking, power on the new (09+) bikes is on another scale compared to my old bike! Brakes and clutch take less pressure, ABS, better cruise control system, more power, the extra gear in the tranny, etc. OF course a new, tight, low/no miles platform compared to an older many miles platform, what would you expect?

I ended up finding a used 12 Ultra Limited, and after beating on them for a while finally got a decent deal on it. Has the 103 engine so a little more torque than the 95. Eventually will stage 1 it an add a tuner to bring the exhaust temps down (one thing I DONT like compared to my old bike - runs a lot hotter).

Originally was gonna keep my bike no matter, maybe turn it into a bar bike or something, but ended up selling it cuz it never got ridden - the new bike was that much better (to me).

Course I have more money tied up in the newer bike, but would have spent quite a bit upgrading the older one as well. And "if" I ever sell this one, should bring more (% wise) than what I would have sank into the old bike...

So that's my story.. If you can part with the $$$, a newer bike will be a better ride. Whether it is worth the investment is an answer only you can make... Good luck with whatever you end up with!

 

Hillside Performance-talk to Scott. 98" kit from them is about $600, Andrews cams to match is about $250, SE upgrade cam plate and oil pump is about $600. Just make sure you get the roller chain for both inner and outer replacements.

 

Keep your old bike : it loves you. I assume its paid for, the money spent will be up front, but gonna be cheaper than a new bike

 

There is a lot more to keeping your current ride. Insurance is less, your bike now is probably paid for and it's yours. If you did the 95" kit with heads and a cam you would have MORE power than the current 103's. You could bore and stroke your 88" to make a 103" and have more power than any HD model. Yes it may cost you 3-4K but you will be happier. Plus your Roadking won't puke coolant.

 

$2200/$2500 compared to monthly payments and higher insurance costs.
Plus, your bike looks great and with the mods your are considering it will haul ***!

 

Keep the old bike a talk to fuel moto for more power... The new bikes are not must faster.. working the 88 will make the bike way more fun

 

Had my 88 in for a 95 build. Took all summer so I picked up a 103. The 95 has a carb so its starts quicker and while not broken in yet seems just as quick if not more so than 103. The clutch is a lot harder to pull now, not sure why. I just may get rid of the 103 and payments.

just to note, the 88 had 53k when it crapped. The service manual mantainance section ended at 50k. Coincidence?