Looks like you might run into issues getting the drain plug out and in during oil change. Play it safe and swap it out and add skid

I HATE it when people cross post the same question and photo in every damn jeep forum they can find. See my response elsewhere.

If you're not planning on going on a road trip and are just DD'ing it, you're probably fine to leave it for a while - just check it frequently to ensure it's not leaking. But it's possible that the moment you take that bolt out for an oil change, that it won't go back in and seal things as it currently is.

I banged up the shit out of mine a few years ago right before a 8,000km road trip. Even though it wasn't leaking, I bite the bullet and changed it. Just so easy to **** the engine if something goes wrong there that you don't notice in time.

There used to be a company that sold aftermarket oil pans that is also a skid, and holds more oil.
Can't remember the name of the firm, or if they are still in business. But as you have to replace the oil pan, and also buy a skid, it might be a great option.

Just remembered, the company is Benchmark Designs.

Ditto.

If you're taking your Jeep anywhere offroad where there are rocks and stumps WITHOUT one the biggest bang-for-the-buck in terms of protection items, i.e. an engine/transmission skid, you deserve what you get. ;)

Ordered a new one from rock auto be here in a week. Half the price of what the dealer wants here in Canada even after exchange/shipping and tax. Going to install it then fab up a skid.
Thanks for all the helpful responses.