MacBook Pro vs MacBook Air

Seems to me a MacBook Air fits those requirements nicely. You can also avail yourself of Apple's one-on-one customer support phone or chat line so you can discuss the ideal configuration for your needs. They don't work on commission so there's no sales pressure.

Start here: https://contactretail.apple.com/Help and click the Connect With A Specialist button.

If you are planning to drive multiple external displays, you will want one of the 14" or 16" MacBook Pros that uses a Pro or Max chip. All Mac laptops that use 'base' M1/M2/M3 chips support only a one external display.

There's a comparison tool that you can use to see the features of up to three models side-by-side.

Apple – Compare Mac models

If you're trying to save money, you may want to get a good 27" 4K monitor instead of a 27" 5K one.

You're welcome Brett. Since it is so portable I find myself reaching for the MacBook Air more than anything.

It seems you like to keep your Macs a long time. In that case you should seriously consider equipping it with a generous amount of storage and memory. If you do that, it should serve you for at least as long as your iMac has — a decade, if not more. The Apple Specialist will help you decide.