Now for the meat of the project - the work!
I ended up doing the work over the course of 3 separate days (and then a few clean-up bits on day 4), however those days were not back to back and I ended up doing the work over the total of a month or more.
The first day was most of the disassembly. I say "most of" because the only item that I didn't get disassembled ended up being the cam bearings (more on that in a bit).
Really, this is simple to work on. Within the first hour or two I had most of the basic support/motorcycle related disassembly done. Tank off, air cleaner off, saddle bags and related things off, exhaust off. All of this was very simple and straightforward.
The base engine disassembly was also not difficult. One note I had was that Harley didn't seem to have much consistency with hardware. By that I mean there's use of allen heads, torx, and standard hex bolts. Although the work was easy I ended up needing a wide variety of basic tools to do the job. I think every drawer in my toolbox got opened at some point, and standard sets didn't necessarily do the job, at least not well. For example the left side allen head bolts for the intake manifold needed a particular size allen key to get to (a socket wouldn't have worked).
Harley makes a number of special tools, but I didn't find I needed any of them except for the cam bearing tool. There's a special tool for locking the cam and crank gears, for instance, but as an alternate you can put the motorcycle in gear, hold the rear brake and use that when loosening and tightening the cam and crank gear bolts. Similarly the aforementioned allen head belts for the intake manifold, Harley makes a special tool for it but I was able to make the correct allen key work.
The cam bearings are a known issue on these Harley engines and S&S includes a new set of cam bearings to install. However, to pull them you need a special tool which I didn't have. Which ended the first day's work. I also noted that the rocker box gaskets and breather gaskets were not included in the kit from S&S, so that necessitated a trip to the Harley dealer before I could put it back together.
The cam bearing tool I ended up having to order twice. The first one was falsely advertised as working for my engine (Harley has different cam bearing sizes, so you need the correct tool).The second time around got the right tool. Really with the correct tool, it's very simple. Tap the tool in, pull the bearing out. Put bearing on and push it in, and it will seat at the correct position when fully tightened and bottomed out.
Reassembly I was hoping to be a single day, but it stretched out over two days. There wasn't any real blocker that stopped me at the end of the first day, just that I knew I wasn't going to get the work completed and had reached a good stopping point.
None of the assembly work is hard, but there is a lot to do and so taking your time to do it carefully and right is slow going. I had never filed piston rings before but it's a simple enough job to do. I ended up getting the ring clearances essentially in the middle of the tolerance band (they say to aim for the loose side if you're racing, which I'm not). Harley has interesting torque specs and sequences on basically everything, all called out in the manual. How necessary those are is a good question, but it seems like with an air cooled engine that has a lot of thermal gradients and changes that it makes sense. There are a lot of areas where you're supposed to make clearance measurements, but I didn't find any of them to be problematic or requiring of adjustment.
By the end of day 2, the motorcycle was looking a lot more like a motorcycle again, but still needed the rockers installed and pushrods adjusted, exhaust on, top end fully reassembled.
S&S includes adjustable pushrods. What they don't tell you (at least not clearly to me) is that the adjustment part needs to be pointed down. I figured that out the hard way, you can guess how.
But the adjustment of them is simple - get the ends touching the rocker shaft and the lifter and then another 4 turns tighter to compress the lifter. They say you're supposed to wait 30 minutes before adjusting the next one on that cylinder, but really that's not a big deal because by the time you're adjusting pushrods, you have a lot of other things to do in parallel. So I adjusted each pushrod and then continued work on some of the other clean-up items.
Although the manual says you're not supposed to turn the engine over using the crank or cam gears to find TDC, I personally find that method to work a lot better than putting the bike in 6th gear and rotating the rear tire.
The oil cooler was the easiest part of the whole installation. Other than needing a 7/16" allen head (I used a spare 1/4-20 bolt in reverse for that), that didn't take any time at all, and is attractive but subtle. I'm glad to have that - I always felt that even stock in the Kansas heat the bike could've used an oil cooler. With the extra power, it'll need it even moreso.
To be honest, the hardest part with the whole thing was getting the exhaust Y-pipe on the engine once everything was torqued down and that was ready to assemble. S&S has the Y-pipe as a single piece to the collector, so with the way the exhaust ports are you have to pull and stretch the Y a bit to get it on. This is a lot harder to do as part of an install than a removal and I ended up messing up two exhaust gaskets in the process (fortunately I had a total of 4 included).
At the end of day 3 I was ready for the exciting part - first start! The first attempt was a failure... because I forgot to hook up the fuel hose. Oops. Once I did that, it started right up and ran quite well. The system sounds great and the engine has no leaks and makes no funny noises, so it seems like I couldn't have screwed up too badly! I've left the shiny coverings for the exhaust off. For the dyno tune they'll need to drill holes and install rivnuts for the AFR readings, so the shiny parts will have to come off anyway. I can just deal with those afterwards.
The morning after I got first start done I finished up some clean-up items - just getting the seat on the bike, side panels on, and other bits so that it's 100% ready to go to the dyno. Tomorrow I'm going to call and schedule the dyno tune, hopefully either sometime this week or next week.
We're also planning on mixing some fun things in a few weeks - once the dyno tune is completed and the RV is together we're planning on trailering the bikes down to the Branson area for a weekend doing some fun motorcycling. That'll be a good break-in post dyno tune and should be a good opportunity to get the real feel of the improvements figured out.
Overall there is nothing about this job that's truly hard, that exhaust Y-pipe was really the hardest. However this is one of the jobs I've done that's used the highest quantity of tools I own for the job. It just needs a lot of different sizes and types. With the clearance between the frame and the cylinders I even had to keep switching back and forth between just a socket and a socket plus extension for torquing the cylinder heads down. I don't see a reason why someone inexperienced couldn't do this if you took the time to follow instructions and not rush things. However winter would definitely be a better time to do a job like this, because if things spread out time wise (which they tend to) you don't end up missing out on as much of the riding season.
Next up: dyno tune!