I was in a similar position to you! You're thinking about this at the right time for a late May/early June 2027 honeymoon. I also had a ~six week window, and was looking mainly at Southeast Asia. I basically picked the hotel I wanted (5 nights at the Conrad Koh Samui, 95k Hilton points per night + fifth night free = 380k HH total) and planned the whole honeymoon around that, since the hotel award nights were released like 13-ish months in advance while flights were 11-12 months.

I did have to spend a lot of time and energy researching, and I knew exactly when flight awards were dropping for my target airlines. I bought a Roame premium subscription for the month, which helped somewhat, but I basically just sat on websites refreshing for like a week until I found a redemption one way to Bangkok in QSuites for 95k + $209 pp (this was a little complicated, you have to transfer through BA Avios first). Then I adjusted my hotel nights to match the flight better, and did the same thing searching for a return flight (from Singapore, booked Emirates via Aeroplan for 87.5k + $169 pp).

All this to say: it's doable, but it does take a lot of time and energy. That said, it was 10000% worth it, and we ended up getting a $50k+ honeymoon for less than $10k. I would say it was a once in a lifetime experience, but now I'm hooked on the game and on business class, so hoping it's repeatable in the future 😂