Ride specific answers below (not to be mistaken for Ferry/Train logistics).
Meeting point? In Brussels the meeting point is La Chaloupe D'Or on the 'Grote Markt' (Grand Place). Directions are in the image and gpx is attached.
Note the detour via Manneken Pis
You can shortcut into the 'Grote Markt' by walking, you'll be drawn into it.
Depart from somewhere at a particular time!! 12 midnight or when everybody is present whichever comes first.
Stop in Ghent. Set fire to tramlines. Stop will be 8km before Gent, friends of the family are putting up a middle of the night stop for us. They have asked what we'd like to eat and how they like to cook and bake. My initial reply was: 'as flemish as possible'. Hope you'll agree
.
Coffee in Bruges. Possibly, see how time goes. BalkanExpress would love to show off Brugge and do a mini tour. Going through Brugge when the streets are empty is a treat! Can't wait myself. It might be an incentive to get going along the canals all else (mechanicals/weather) being equal.
Ostend for Breakfast. Definitely, either Vismijn Kanteen or Patisserie on the other side of the port. De Vismijn Kanteen is an unknown, looks like it might serve beer at all times but TBC (for those who are interested), and I've been told not to go there on my own. Well....
Again, the ride is not Friday but SATURDAY 3rd May, arrive in Oostende on the Sunday morning. It's the weekend of the first May Bank Holiday.