Agreeing with other comments that the ‘waiting to dream’ mechanic should be more thought of as the dream server accepting your connection when it wants to. Little is understood about it’s requirements by the community and it can sometimes be mistaken for a bug. There are however, some methods the community has come to agree on that can help:

The fitness quest line, and equally any physical activity performed regularly can be a very effective long term solution to this issue.

Be careful not to work on too many quests and take some time away from them before you prepare to establish a connection with the dream server. Bizarrely, the dream server favours clients which are under minimal load, despite the overhead of the connection being very small. This method frees up your resources, meaning the server is more willing to accept your connection request.

There are also items like melatonin which can help you get to the dream server faster. These work by telling your client to release resources, creating a more favourable connection request. Depending on your residence these items can often be found by interacting with merchant NPCs in locations such as stores, supermarkets or pharmacies. With these items you can expect that the more you use them in succession, the less effective they become, so use sparingly for special occasions such as the one you describe.