I'm in a similar place. I do small scale biointensive urban backyard gardening, but it's almost certainly <1% of our annual food intake. Even with an aggressive preservation programme (freezing, canning, whatever), I can't imagine it really making a dent in our overall food footprint.

One thing I want to improve upon is staging plants, even plants of the same type. It doesn’t help if almost all of my cherry or heirloom tomatoes are ripe in the same couple weeks.

I’ve moved this year and have a bigger yard but too many trees for a garden. Trying to figure out where I can squeeze plants. What do you mean by biointensive?

See: https://en.wikipedia.org/wiki/Biointensive_agriculture

Companion planting and composting is most of what we do. Also just overall density— for example, we have probably 2-3x the recommended number of tomato plants in a 4x10 raised bed, and are managing it by aggressively cutting back blighted leaves and controlling sucker growth + providing lots of physical support for the plants themselves.

Agree on staging as a challenge; I haven't figured out a good system for that. Conventionally, preserving has been the answer, but it's a lot of work to make that much tomato sauce and salsa, and better hope you like it if you'll be stuck eating it all winter!