I'm just starting to sleep in diapers regularly. Though I've done it for a few consecutive nights in the past, my current goal is to spend every night in December diapered.
Getting used to the bulk is not easy, especially because I sleep on my side, and I've woken up early a few times.
But I always start the night dry, not wetting until the early AM hours. Being wet when going to bed is just going to make it harder to acclimatize - there will be more bulk, and skin irritation. I'll be twice as likely to wake up at 3am.
In my admittedly non-expert opinion, going to bed wet is an considered an advanced technique - to be approached only after several months experience of sleeping in a diaper most of the time. Get some experience points first, then go up a level.
Something to look forward to, ne?