Hitting the "Upgrade Wall" with New Mac Laptops?

Between my family and I, we're in potentially triple-digit mac products over the last twenty years. I say this to demonstrate my familiarity with apple and with iOS.

That said, I cannot decide which Apple laptop to buy right now given all the rumors being thrown around. I'm hoping someone has a minute to lend me some advice?

A little context:

Previous Mac: Souped-up Macbook Air 11-inch with 500 GB storage, 4GB RAM (3 years old, broken mouse).

Potential New Macs:

-Souped-Up 13-inch Macbook Air

-Souped-Up 13-Inch Macbook Pro

-Wait for New Macbook Pro?

Uses:

Light gaming (Starcraft, Diablo, Borderlands, Civ V. Not a graphics-focused gamer, would like to run Civ VI).

Photo Editing (RAW, but no plans to shoot 4K or 5K)

Large File Transfers/Downloads (Frequent downloads of large folders with lots of scientific journals, massive Excel spreadsheets, other science work-related stuff)

HD Movie Viewing (hence 13-inch over 11-inch)

Finally, I travel constantly and my laptop rides with me on a bike. Durability is a premium. Is the Macbook Air any tougher than a Macbook pro?

My reaction in the past has always been to wait for a refresh. However, I think I'm seeing diminishing returns on upgrades. If I get a really nice 13-inch Macbook Pro, am I really going to hit a wall where I will wish I had waited for the new one, given that I do zero video editing, no hardcore gaming, no boot camp, no 4k photos?

WWYD?