Opinions needed

Bones
Just a bit more info, Are you looking to hop the engine up to 95 Inch or Larger?

What's the budget if you don't mind my asking, there are a lot of budget ways to hop it up, depends on the goal...

All those kits are great and the good thing is everything in the kit is designed to work together, cams, heads, pistons, etc.

But you can do it yourself for maybe a little less money..

The old saying "how fast you want to go?. well How much money do you have" still applies...

The hop up gamut runs from bolt on bolt in and tune to a full build stroker.

95 to 98 inch kits are simple bolt together kits, reliable, make good power and can be stretched to make wild power.

Remember with massive power comes more expenses - Drivetrain, as well as shorter life.

Oh don't forget brake upgrades, you get more go you need more whoa!

A 95 kit can be done in a weekend by a shop, a good wrench or a bunch of guys in a garage that have some knowledge of tools and engines. These are tractor engines and not that difficult.

Because you have an 88, anything over 98 is going to require splitting the cases and in some instances splitting, boring, upgrading the main bearing to a timken because your cases have a bearing that can't handle serious power.

The HD 103 bolt on cyl/pistons won't get you to 103 because you don't have the stroker crank, the 96 has the stroker crank already.

Hopefully this will get you thinking in the right direction, I have a lot of ideas on things to do, it's just how involved do you want to get and how much power are you looking for in this project.

If you have a buddy that's whipping up on everyone, well, then lets find out what he's done and build a nice sleeper to whip him stop light to stop light.

Or do you need more power to pull two up and cruising but don't care about tire shredding bottom end power...

Not trying to slight your question but lets get a little more specific on what you're willing to get into, a $9K stroker build with high po drivetrain and PM brakes or a couple of grand on a nice hot 95 inch engine.

Finally, how fast you wanna go? How much you want to spend....

I think you could do it for less than 4K based on what you are saying you just need a good strong midrange engine to help with passing, riding two up, all the basic stuff not a brow beater. Good now we're getting somewhere.

There are a ton of good kits out there, HQ as mentioned above, SNS, Axtell even HD's hop up isn't bad for what you want.

You said you don't or can't wrench on it, so have you talked with any local shops about what they will do and how much it's going to cost for them to get you the kit and the labor.

Compare that to having your stock heads and cylinders machined to 95 inch, street port and clean up and dropping in a nice mild street cam, then getting it tuned. Probably in the under $3K range, labor, gaskets, materials and work....

Talk with Amy and Bill at Bishop's Performance - Parts & Service for Harley Davidson, Buell, and other American V-Twins they are in Detroit and have a good rep with doing this and Bills a very good tuner. You could trailer the bike up drop it off and have them do the work..

Well one reason is for $4 to $5K I could build an engine that will flat whip the 96 inch engines butt

Actually I could build an 88 that will smoke a stock 96 for under a grand...

FYI check the HP and TQ ratings on the 88 and the 96, they make darn near close to the same HP and the 96 only makes a little more TQ, it's not that big a difference, although you would have a new bike...

Yeah, lot of folks think the new 96 and 110's are stout, when compared to a stock 80 evo, they are, the 88 is anemic at best but the 96 is a dog compared to what it could be.

Most 95 inch builds even mild ones running around will stomp a stock 96.

I've put a woods 6-6 in my friends 07 FLHX and it runs way better (tuned too) with stage 1 pipes and air box than a stage 1 96, and it even kept up with the new CVO Ultra 110....

OK, I got to throw my 2 cents worth in, even if its not worth 2 cents to some. I'm not a mechanic but I have done a lot of work on my own bikes and know a lot about the different years of motors from 99 to present. I've done the 95 kit on a couple of bikes with cams and I can say that my 09 with the 96 motor, pipes and a stag one kit is stout and goes a hell of a lot stronger and better than my old 88B with stag one and pipes. For me I see no reason to go to a 103 and cams in it when I can also get to 90-100 really quick the way it is. This is the first Haley I've owned that I don't feel the need to pump up the motor any more than just the stage one with pips.
Now my 01 Springer could really benefit from a 95 upgrade.

VooDoo
For me, I like the same, a sleeper, looks stock but runs like stink!

Heres' a little recipe for a very stout 95, one that will run good, get good mileage, and when you crack it get the tire spinning very easy, it will suprise a lot of folks...

95 inch HD 10.5 to 1 pistons (although with todays gas 10 to 1 might be better)
Bore stock cyl out to fit pistons
Heads- Stock send to Bill at Bishops for stage 2 work, larger valves, clean up intake and exhaust, send intake for same work to match it up to heads and for flow testing.
Cam - Woods TW-6H .590 lift, advance it 4 degree (gear drive is my choice if you have an older twin cam (newer tc's just can't be gear driven reliabliy due to crank run out)
Adjustable ignition for Carb or Powercommander for EFI

Exhaust - THunderheader or supertrapp supermeg disk. (depends on your idea of noise)

I was pulling 105/110 with this in my heritage, it's not an overly expensive build and will flat run, you'll have a bit of valve train clicking but nothing major... Woods cams do that.

That's why with the ethanol I was saying you might want to go 10 to 1

As long as you run good quality super unleaded you should be fine, you can run the 6h woods cam straight up and drop compression as well...

That was on my 00 Heritage and it rocked no knock, and started without comp releases.
and the stock starter.

Although I would put comp releases on it if I did it again.

Injected is fine, I would put on a powercommander 3 usb and have it dyno tuned or, a pc 5, dyno it and then add the auto tune which adjusts the map based on riding conditions.