During the weekend the parking gets full very quickly. I'd advise going as early as you can, otherwise you might have to park on the street and walk down! Have fun!

yes. parking is an issue though

It's a beach. There is no floor

It’s still Lake Ontario but it is swimmable. There’s also a nice beach there

Congratulations....proposing is a good idea, however, to walk about 5-6km might be a bit too far and I don't think there's any day/night restriction with time to access the beach are...however, walking in the dark is romantic, but not a good idea though :)

As far as I know the foot of the Bluffs beach is a park. You can take pictures of anything you like. A permit may be required for an actual wedding, but personal pictures are your own business. The top of the Bluffs is more tricky because most of the areas are in private hands. Exceptions are Sylvan Park, Cudia Park, South Marine Park, and the Guild Inn park which has neat remnants of old bank buildings etc. If you want the Bluffs as a backdrop, then the foot of Brimley Road is your best bet. Did you know the TTC now runs a bus down the hill?

Yes there is a lovely restaurant overlooking the lake, but it is not cheap. Others have answered you about the stroller -but \i think it is up to you how rough a terrain you and baby can stand

There’s no any bike rental place around that area