I first tried attempted the walk from the Monorail out of curiosity - my first two stays at this hotel were longer stays with the family and I honestly felt like I did the walk between Shimbashi and the hotel a thousand times. So when I returned to the hotel without family, I was keen to try an alternative way to get there that didn't involve Shimbashi.

While the walk from the Shimbashi to the Conrad is definitely shorter than from Hamamatsucho , the shorter travel time on the Monorail means that the overall travel time (train/monorail + walk) is not that different. As per the Haneda Train & Monorail access site (https://tokyo-haneda.com/en/access/train/index.html), it takes 13 minutes from Terminal 3 to Hamamatsucho on the Haneda Express Monorail - on the Keikyu line, it takes 13 minutes to get to Shinagawa and both Google Maps & the Route/Fare search on the Keikyu website (https://www.haneda-tokyo-access.com/en/) suggests that it's another 8 minutes from there to Shimbashi. I should note that the Express Monorail services don't run at all times of the day (see https://www.tokyo-monorail.co.jp/eng...able/1120.html), but between 9am and 5pm (on weekdays) the 8 minute time saving on the Monorail is a solid equaliser.

That said, the walk from Hamamatsucho is almost entirely exposed, so on a rainy day I would always take the Shimbashi option.

When I first researched the Monorail option, Google Maps indeed suggested the transfer from the Monorail to the Oedo line at Daimon. However, I'm the type of person who would rather walk a slightly longer distance than transfer between transport modes, as such transfers can involve a fair bit of walking inside/between stations (including potentially for waiting for lifts/elevators with luggage etc.) and may also be convoluted as you say - my preferences combined with the aforementioned curiosity meant that I was always going to skip the Oedo line transfer on the first attempt of the Monorail option (and will continue to do so).

On the difficulty of the walk, having researched this particular thread ahead of my very first to Conrad Tokyo (and having taken another look before before this most recent stay), I think it's fair to say there are people who don't find the walk from Shimbashi to the hotel particularly easy. I certainly found the step-by-step instructions from Shimbashi very useful, and I'm fairly certain I would've had to ask for directions without them (I reckon knowing to turn right when you hit the two Family Marts is the hard part!). So while I'm not at all suggesting that the walk from Hamamatsucho is particularly easy or easier than the walk from Shimbashi, I want to highlight to the community that it is not overly difficult either - my follow-up post will include some instructions, which hopefully other forum members with preferences similar to mine will find useful.