Expensive hotel special occasion

[14February2021]

I'm looking to book a hotel suite for a few nights in October.. its more than I'd ever normally spend but it's a special occasion - do I...
Book a flexible room and keep an eye out to see if they drop the price closer to the date or just book the cheaper advance price right now?

This far out I would book flexible rate and see closer to date if there are any promos with cheaper rate.

Yes! That what I thought was overthinking! Thanks!!!

Book direct with the hotel, not through a third party such as Booking. The hotel might have special offers such as arriving on a Sunday, which is often cheaper than other nights.