I have been through them all, omnifocus, things, 2Do, etc. I have gone back to Apple reminders and it is actually sufficient for me.
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lucky 
i’m at Apple Reminders right now. Although something more powerful would probably fit my needs better, Reminders is free and very hackable with Shortcuts. That’s why I like it.
I love NotePlan. Looked at Agenda and the others and have come back to NotePlan. The fact that it’s on both IOS and Mac, and uses Markdown is awesome. I like the daily journal pages plus notes for Project Tracking and notes.
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I would also look at getting by with just a good iPad (with any keyboard/mouse combo) instead of a Macbook. The current iPads are usually more than capable of running what you need. Getting an old macbook will probably rule out running the latest software, and that will degrade your user experience.
Not broke but a retiree. So I started with paper and pencil. Graduated to DayTimers planners (which are still made), then a Palm Pilot, iPod, iPhone, the electronic ones with sync to a desktop app.
I still use Reminders, Calendar, and Notes. All free once you buy the hardware. I also use Omnifocus, but for long term repeating reminders like change the furnace air filter and stuff like that which just need to be written down somewhere. I suppose I could just do all that in Calendar and probably would if I hadn’t already bought Omnifocus years ago.
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I have an old MacBook and a iPad. I installed macOS Catalina on it with the dosdude1 patcher. Anyways, I do a lot of stuff you can’t do on a iPad
It’s all based on your use cases. I’ve found most of what I do can be done on an iPad. Mostly certain coding Its not easy to test or even run on an iPad. I found this Youtube channel where the creator codes using an iPad.
My use case is when I’m mobile I can do everything I need to do on an iPad and when I’m home my desktop mac can do what I can’t do on the iPad.
That’s really interesting. I also do a bit of coding, but for me, it’s about being able to create windows and Linux installers. iOS is a great platform, but I just can’t do everything on it. I also do a bit of gaming, and I frankly don’t know how I could play portal or DiRT rally on an iPad.
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I vote for this too.
My very first reason to choose Org-mode with Emacs is very niche: I’d like my tools to have Vim keybindings, and Emacs can provide that with one of its package called evil.
If OP decided to try Org-mode, iOS app to manage task from Org files is Beorg.app. It’s not too easy to learn/use, but it fulfills my needs.