Should I start looking for a job now or wait until January?

I am currently employed full-time in a remote/work from home position. I have been turned down for promotion for 3 different internal positions in the last 3-4 months.

I was passed over in for the first two positions for employees who wanted to return to their old roles in the company. I completely get this from a company perspective, because you don’t have to put in any or much work training them. The last rejection is the worst. It was within the department that I currently work in. I was turned down for a coworker. In my opinion I was more qualified. I have more experience and I have a Masters degree related to the field. I also get along well with the team the position was on. Every time I was rejected I was sent a personal email talking about how very qualified I was for the position, but they went with someone else. This time I asked my supervisor (who isn’t responsible for hiring for that position), why they keep telling me in these emails how awesome and qualified I am, but aren’t promoting me. She said I should apply to other positions that would be more of a challenge for me.

I am not being told that I need to improve on anything, gain more experience, etc in these emails. I exceed expectations every year. Honestly, I just feel like aiming for meets expectations. Everybody got the same raise regardless of how they did this year. We were told raises would be based on how we did, but they weren’t.

I just am hearing that people don’t really hire in October, November, and December. That most companies are working on their budget for next year, then start hiring in January. I also have a family trip planned for late January. My 401k is fully vested.

Any comfort, feedback, or advice is welcome.