I've only recently been focused on optimizing my miles. We travel a lot personally and a decent amount professionally. I'm focused on accruing useful miles and have already taken a few flights I wouldn't have picked to get more useful miles. But, I'm kind of stuck in a non-hub city and my international travel often means I have to book the flight that fits my work schedule the most. See me having 20k points in Emirates that are kind of stuck.

We have about 300k miles between Amex and Cap One. Another 40k in Chase. Another 150k in United. And 10-20k in Delta, Emirates, etc.

All that said, I'm planning a trip to Hawaii with my wife. Flights are either out of our price range for business class from the east coast or just not good redemptions for economy/premium economy. However, I've found a great redemption for two Hyatt properties that would allow us to book a $1,000+/night room for 25k points per night.

What I'm struggling with is international business class travel would take precedence over hotels for me. Every time. But, I've been looking for business class award travel on some of our considered trips (Bangkok, Singapore, Cairo) and haven't found anything remotely affordable with our current miles wallet.

I know it's a personal decision for everyone, but I'd love to hear some opinions on what you'd do, what you did in similar situations, anything I'm not thinking about.

A good rule to keep in mind is that points rarely appreciate in value, but frequently depreciate.
As to when to use them, though, you're right that it's a lot of personal preference.
-Some people prefer to use points on aspirational redemptions --luxury hotels and business class that they would never pay for out of pocket
- Some people use points whenever doing so would exceed a certain monetary value. (A lot of blogs/sites have estimates of how much they value certain currencies).
- Sometimes people want to bank up a large amount of points for a specific redemption, so it makes sense to wait.
- Finally, a lot of times it makes sense to use points when the cash options are particularly high in a given route/location

I find myself engaging in a mix. My Delta miles, for example, I tend to use whenever I can get a value of more than 1 cpm. My United, Aeroplan, Amex, and Chase points, I save up for long-haul business class travel. For hotels, I have been trying to burn Marriott points whenever I can get value of more than .7 cents per point because I have had so many bad experiences with Marriott of late that I want to be done with them. I'm basically burning Radisson points whenever there is a chance because the program has gotten complicated and not worth the time.

Those EK ff miles will expire if you do not use them. Look at EK ff partners. https://www.wheretocredit.com/emirates
-->Miles/Points that Do and Don't Expire

Thank you! It's helpful just to hear how others work through it. You see so many travel bloggers armed with massive pointloads from credit card referrals and insane churn. I'm just trying to churn cards a bit and be a bit smarter about the miles I get through my professional and personal travel.