Updates, interface, ease of use stuff, typical noob stuff (i think)

I came from a Mikrotik router to a linksys WRT1900ACS
Mainly because the mikrotik was the last gen that didn't have AC and i won the linksys on a twitch stream; i've got AC on the pc i use.
So i knew right out of the gate how bad linksys operating systems are and jumped onto OpenWRT.
Right now i'm a complete nooblet, i installed the firmware, then found out you need to ssh, or at least i didn't see an option to use an interface on first try.
So i installed Luci as per a quick google search on GUI for OpenWRT.
From there i've really not done much.

I like my routers to have the functionality that later i can play with; mostly by google searching what i don't know set things up, then forget about them completely.
In that state of mind, i don't exactly know how, when, or where to look to keep up with updates.

If you're at all familiar with RouterOS, you know there's a ton of features in it, but they also have the quickset where you can click "check for updates" and read what fixes they have done.
Is there something i can install that would give me that with an easy update option where it downloads what i want to update via a button, maybe some check marks if there are multiple packages that are there to download, and then push a button and let it do it's thing?

If not, can i get a quick rundown on what i should be doing to keep this up to date?
also any recommendations for additional cool things i can install that would be nice.
Not even sure if there's functionality for the usb to work. Would actually like to set my usb drive on there so i can have a network drive that isn't next to the computer and my mobile devices could pull/push to.

Yes, LuCI has this functionality by default. Once it is installed, just go to:
http://192.168.1.1 (or other router IP that you have set)
...with a browser, that is connected to one of the LAN ports and look around the interface.

You can also do the same from the serial interface I assume you are using:
https://wiki.openwrt.org/doc/techref/opkg

It is however not recommended that you update your router in this manner. Embedded devices that work as they should, should not be constantly upgraded. The filesystems in use in OpenWRT will cause additional flash space to be used when updating and the system will become less efficient. If you must, reflashing the entire device is a better option.

LP,
Jure

Especially given the recent vulnerabilities of Mikrotik, you're probably a lot better off with OpenWRT!

On updating, while updating a package or two from time to time to resolve security flaws makes sense, the preferred approach is to update the entire image. You can download a new image from https://openwrt.org/downloads and flash it through LuCI ("web GUI"). Downloading a backup prior to flashing is a good idea. You'll have to re-install any packages you added after the router reboots. I don't know that there is an easy way to do that re-install through LuCI.

There should be a new "stable" release coming in the next month or so. I'd definitely recommend upgrading to that. Now that OpenWRT keeps more up-to-date than it did a couple years ago, I generally update the entire image every few months, or any time there is a notable security flaw identified in the Linux world or the packages OpenWRT uses.

If you have more than a couple tiny packages that you install, building them into a custom image will ssave you space and ease upgrades. Some use the "Image Builder", but I prefer building from scratch. It does require a Linux system (never had much luck with macOS), either on its own box, or in a VM. It takes me about 30 minutes on a modest box to build the first time, much less for subsequent changes.

Personally, I don't run any more on a publicly exposed box than I need to, for security reasons. Others have different opinions and practices on this. Yes, you typically can mount a USB stick on a USB-equipped device. Samba is available if you trust SMB security. I'd think twice about sharing on the "WAN" side. You might want to consider something like NextCloud running on a machine inside your firewall and "port forwarding" to it, perhaps a VM, Raspberry Pi, ODRIOD, or the like if you don't have a native `nix box already.