This is such a pain and ripe for disruption. No company has gotten it right so far.

First I look at flights: what is affordable and when? Some dates are much more expensive than other dates.

Then I look at hotels and itineraries: What do I want to see? What is affordable near where I want to visit? Hopefully there isn't a convention that overlaps.

Finally I look at rental cars: Is it still affordable?

Recently I've used the packaged deals websites or through the airlines. It can be cheaper to get it bundled.

If any one of those factors (airfare, hotel, or car) is overpriced, then I look at a different place. It is usually conventions that disrupt my plans and cause spikes in the prices.