I've also just embarked on a Di2 upgrade, although not for Tri.
My first recommendation is to build a spreadsheet!
My winter bike already has 105 11spd mechanical so crank, chain and cassette are being retained for now. I went this route:
| Description | Part Number | Option |
| Shifters | ST-6870 | |
| Front Derailleur | FD-6870-F | |
| Rear Derailleur | RD-6870-GS | |
| Battery | BT-DN110-A | |
| Battery Charger | SM-BCR2 | |
| Junction Box A (Bar End) | EW-RS910 | |
| Cable - Junction Box A > Shifter | EW-SD50 | 350mm |
| Inline Wireless Adapter | EW-WU111 | |
| Junction Box B (4 Way) | SM-JC41 | |
| Cable - Battery | EW-SD50 | 600mm |
| Cable - Front Derailleur | EW-SD50 | 300mm |
| Cable - Rear Derailleur | EW-SD50 | 600mm |
| Shifter to Shifter Cable | EW-SD50 | 600mm |
| Shifter to BT Cable | EW-SD50 | 300mm |
| Junction A to B Cable | EW-SD50 | 1200mm |
You can do it differently but I wanted the bar end junction box and clean internally routed cabling / battery.