Best brand tool ecosystem to go with?

My Ryobi tools feel cheaper than my DeWalt ones imo

I wouldnt start over but I've been pretty happy with Milwaukee. Just got the 18v brad nailer this weekend and it is fantastic.

The battery ecosystems are so cheap to get into these days that you really don't need to stay with just one. I have Dewalt and Ryobi. Ryobi just makes some tools dewalt does not and they also are cheap. If I know a tool is getting heavy use I get a Dewalt version, if not I might get a Ryobi depending on price. I have never had a Ryobi fail me, I have had dewalt fail me but they replaced without any dumb questions.

If I just stuck with Dewalt, not sure if I’d go with the 60v cordless trimmer or if the 20v trimmer would be enough for my ~1 acre yard

Either way, I assume I’d need to get the bundle with battery as the 2 20v batteries I have with the drill set are only 1.3 Ah

Stick with one. It makes keeping up with chargers/batteries much less stressful. Both are decent brands, with the edge (my opinion) going to DeWalt.

I like Makita

Another available option is to stick one major system for batteries and chargers, and use battery adapters to convert other brand tools to those batteries.

You have to be careful doing this to make sure the battery is compatible and where the circuit protection is located. But it may allow you to buy a Ryobi tool at a cheaper cost (or even not available) and use the DeWalt battery. You just need to manage the battery power when doing so.

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I have a 20v Dewalt 1/4” impact drill and driver set with 2 batteries/charger I got a few months back.

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Dewalt tools will last johnny homeowner (like myself) a lifetime. I'm sort of locked into Dewalt, and since you've already started, I'd continue down that road also. Dewalt makes damn fine tools. Are they as good as Milwaukee? I'd say probably not.

I started with a Dewalt cordless drill, then purchased a Dewalt hammer drill. I added a battery or two here and there, chargers, etc. Then I bought a Dewalt grease gun, a 3/4" impact driver (I love the shite out of that thing), angle grinder. I'm fully into their ecosystem and have been for many years.

The only thing they do when I put a battery on and pull the trigger is fire up and work dependably.

tl;dr: Stick with Dewalt since you've already started.

ETA: Also bought a Dewalt pole saw. It actually does a good job, but lacks the power of a gas powered pole saw. It's great for small jobs though. shite, I have a Dewalt sawzall also. Love that thing also. I bought some bone saw blades for it. It does a hell of a job processing deer, or cutting anything else I throw its' way.

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Thinking of ryobi. This all started because I need a battery operated weedeater and ryobi seems to be the crowd favorite. The remaining ryobi tools seem to have solid reviews and like I said, none of them will get everyday use.

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Ryobi and don't overthink it.

Their tools aren't as good as Dewalt (which aren't as good as Milwaukee); but that isn't relevant as you state- you're not using them constantly.
They cost 2/3 to 1/2 the price, and they're plenty "good enough" to do the occasional job.

And it can't be stated enough- Ryobi makes a battery-powered everything. If you want or need some oddball tool, a little clip-on fan, etc, they have one for cheap.

I have multiple tool lineups at home, and Ryobi by far gets the most usage. The only non-ryobi must-have I own is the Milwaukee 12v ratchet.

I figured I'd wear a set out on the barn build and was going to buy a kit anyway, and since the metabo 30° nailer was on special when I bought, I went with them. I dropped an 18v impact driver from the scissor lift and although it still works, the flipper forward/rev broke. I caught the 36 volt triple impact on sale with two batteries and it's a beast. I bought the tin nibbler which has been terrific for coping the exterior PBR Panels. The 36 volt 7 1/4 circular saw is also a workhorse. I've marked the blade offsets on each side for using a cutting guide. My dewalt tools are holding up good, just don't seem to get the battery/tool specials that I can justify. I bought the metabo 10" 36 volt miter saw but really wish I hadn't. My old 12" Porter Cable with laser that is dead nutz is still going strong.