Guess it depends on whether you have anything at the moment?
What are you thinking? You could probably keep your existing cranks so that avoids having to fit a new crank/BB, same with your cassette. All you'd really need is some allen keys to remove the headset and various derailiuers. You'd already got the hydraulic cables for brakes etc too, so just need to swap shifters, run cabling for the DI2 and replace the front/rear derailieur.
Don't think i've missed anything there.
EDIT - Maybe easier to run cables to rear derailier without the BB installed, but my frame has a removable access door thing on the underside that helps with that. Unsure if yours does too?
Main thing is probably how much time you can commit to installing, realising something is wrong, re-doing it before you're happy with it and potentially being without the bike, vs what the bike shop could do in a couple hours and potentially have it back same day. I know with kids etc it can be difficult to spend that amount of time slowly working through it
All points bang on the money. Not a huge amount of tools needed... Hex bolts generally throughout on Shimano, definitely need a torque wrench (shifters to bars/derailleurs to frame/refitting seattube/refitting crank arm).
Hydraulics are fine left as they are - providing you're not moving shifters/changing bars/etc (don't need to change length).
The access door at BB will be very frame dependant on how useful it is. I actually tried to wire mine without removing BB (which I've done a lot of times) but just too awkward to thread cables so ended up removing it. My frame not designed for Di2 so quite awkward, took probably 5-6 hours total, over several nights.
Bettershifting guides are very good and hate to say it - 'it's as simple as you think it is' as well as one of those jobs which seems to take longer than you think. You can't rush it - certainly if you're a bit of a perfectionist, but you also learn a bunch about it (& your frame) by doing it yourself.
Assume I have nothing but a bike stand and basic allen keys.
As for what I'm thinking, whole group set switch. I want easier gears so changing from 52/36 to 50/34 up front and 11-34 at the rear. So I would need to take off and change the cranks.
Would the BB need replacing or can I continue to use the same one? if I look under the bike there is a plastic cap but I've never tried to remove it so no idea what is under there.
You might find your chain cut for 52/36 & 11-32 switching to 50/34 & 11-34 it reaches ok. Not a massive difference in 'gear inches'...
Little plastic cover could be enough, but may depend on your frame. On my Giant and Specialized it is generally there to aid cleaning, so contains a drain hole, so 'sediment' which is washed into your frame can drain out - but if there's a blockage it's easy to get to. Or if you drop something inside... But it's not very big for accessing things. I tried & failed!
Looking at it, i think this is why I decided agaisnt it in the past, I think I'd have to go SRAM Force as I'm not sure where the battery would go. I know the seat tube is the common answer but it seems when from the factory, Canyon do it in the downtube.
Though I suppose if I wanted to do it myself and stick with Shimano I would have to remove the BB to run the cable from the seat tube to the front and rear derailleurs?
Maybe the local bikeshop is the better solution. But I think this is the better long term solution for myself. Then when we have the new house and a properly secured space for a bike I can get an all singing all dancing once then
And I would absolutely need a blanking kit to get rid of the two holes for the shifters.
Fitted my battery in my seat tube. Frame nor seat tube designed for Di2. No problem for a tinkerer... Mine is jammed in there wrapped in bubblewrap, with a couple of zip ties around it so I can pull it out... Secured with a plastic 'bung' (actually a cap from a tube of loctite with electrical tape wrapped around it). No problems (fitted in June 2023).
LBS is 'easier' but it still takes time... Experience helps a little to reduce that, but it's still a lot of 'hassle' so expect whatever their workshop cost is for 2-3 (maybe 5) hours.
I fitted one of the little black covers on my RD cable. Never fitted well and fell off after a few months. Waste of £9. Wrapped some electric tape around it to create my own and keep the wire in place. Left the 2 openings on my downtube open to the elements, figured the water they collect helps clean the internals. Due to my frame colour almost impossible to get some (as frame doesn't have Di2 kit available). Maybe could make something as I did eventually find some nail varnish very close to my frame colour, so just need to cut something to shape and paint it...
Generally - notice a theme here... It's a very good 'learning curve' if you like tinkering and expect to maintain & troubleshoot your own setup. You learn a bunch about it from fitting it, while also specifically fitting it to your 'needs' (and to a finish you're happy with) if you're prepared to spend the time doing it. If you're not the sort of person who enjoys stripping things down 'the process' to maintain and understand them to save some money (like replacing bearings yourself) then you won't enjoy fitting Di2 - your time and money/frustrations are better spent paying someone else to do it!
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