My shocks are pretty bad as well and not running skids either.. got an inch of sag whole way around so I've gotta watch wheel placement for ground clearance.
But surprisingly enough without the skids or lift, my two main problems I consistently run into are caking up the sides of my ******..and my main issue, I like to push her through mud/water thats too deep and flood out my engine bay. Even though youd expect it to be bottoming out, i rarely do. So I have a couple ignition coils and plugs I keep in my toolbox in the trunk at all times..
Other than that, know where your tires are at, at all times and you should be able to clear any decent trail and most of the crappy ones.
I will admit, being 2wd I run into some trails that make me go hell nah, but if I had 4wd I'd just keep on pushin.
It's not about how stuck you'll get, but rather how good you can get at getting unstuck.
All that being said, I'd get the skids first just to cut down on debris hitting the underbody and driveline. But you don't actually
need a lift to off road, so long as you're not afraid to commit to the trail.
But everyone else is going to tell you the lift is a necessity for trailrides, but you stated nothing crazy and slightly beating on it.. so I assure you that so long as you know your liberty it will surprise you offroad.
Even got my girlfriend to admit that my jeep loves mud waaayyyy more than it likes pavement.
As for the is it too late in the libertys life for a lift? I'd say that's all in the amount of rust you have. Everything else is replaceable in a sense.
Been saving for 2 months for my lift in the spring and I'm sure I'll be probably around 215-220k and I'm still gunna be throwing money into a lift and tires. But that's because I got all my rust rid of/neutralized and por15'd the whole underside with a hammered finish rustoleum coating over it.
Only thing that bothers me is my rockers, but that's because they're half fiberglass from busting holes in them lol.. but gunna weld some new ones in come springtime. Only about 150 a piece for them, and I'm just gunna paint them black prior to install, grind back the weld zones, and touch them up after.
So, if you're not rusty, then I say heeellllllllll nah its not too late in the libertys life.
But I think that's just because my view on it is more...well if she dies, she'll be a perfect donor for the next KJ!