The plant looks healthy overall, with the damage on the lower leaves only. I agree with others that it just looks like the plant was bumped around a bit, I don't see evidence of any parasites. I also agree that you will run into issues before long, though, if you don't change the growing conditions. Even when I buy a potting mix specifically for succulents (which should be provide better drainage than a regular potting soil) I cut it in half with perlite. And succulents always prefer to be snug in their pots!

I think your Gollum looks good! Some varieties do have slightly yellow leaves. I had one a long time ago and loved it! If you want the leaves to be darker green...you can always add 1/4 to 1/2 strength of fertilizer once the weather warms up... should green it up a little. I'm not sure what zone you live in? They love full sun also...but if they're not used to direct sun...slowly acclimate it so you don't sunburn the leaves. Wrinkly leaves does sometimes indicate lack of moisture? Can you check the roots to see if its very dry or stick a thin chopstick in the soil to check for moisture. If your soil is very dry, Water it thoroughly...should get rid of those wrinkles and plump them up in a few minutes or hours.

The fungal infection was over three years ago so I doubt it is relevant to whatever is causing his current problem but that was the only time he has ever been sick before. It caused brown spots to form on his leaves and then they turned to holes but i removed all the effected ones and exposed the roots to oxygen and it killed the fungus that was making him sick before. This girl I was rooming with in college at the time was taking botany and she said it was a fungus. Either way everything she suggested worked and he got better. Whatever is wrong with him now is definitely not the same thing but I dunno how to treat him for anything else especially when I do not know what is wrong. I just potted him into that soil a little over a week ago and I waited a few days to water him afterwards. I would have waited longer but his leaves started getting soft, which is what they do when I forget to water him for too long. As for the soil, it's some kind of succulent/cacti soil that comes in a yellow bag from Walmart. It's the same kind I always buy (with the exception of the last bag that had gnats - I got that one from Home Depot although it was the same brand) and he has always done well with it. Can anyone give me suggestions on a better kind of soil to buy that I don't have to mix myself? I live in a one room apartment and it wouldn't be practical.

Jades will loose old leaves, they usually dry up to crisp and eventually fall off (or you can take them off). There could be few at the same time, but usually just 1 or 2. Do you have just few or may yellowing at the same time? Black spots could be oedema/edema, that is a disorder, not a disease. Those spots could be raised, like a pimple, often hard and you shouldn't try to take them off (they would have to be scraped, using bit of force, and would leave wound on the leave). Oedema could also look like irregular spots. If the black spots were oval-shaped and quite same in size, it could be scale insect but I do not think that's what you have. Powdery mildew could also have darker spots, but that is a fungal disease and often covers more of the leaf. It could also be 'fuzzy; - doesn't look like you have that either. If the soil was hardened around root ball, it is likely because it is mostly peat that became hydrophobic. Not best for the plant, since hydrophobic peat is quite difficult to re-wet. Hard as it is, it repels water and regardless how much you water, plants roots can't get any. Since you repotted it with that hard soil on, all new soil will get saturated but roots will stay dry. It is better to get rid of old, hard soil and loose some, even lots of roots. Jade will regrow roots in better potting mix quite fast. The mix should be well draining. You can make it so by adding lots of sifted or rinsed perlite (or pumice if available). Mixing it in 1:1 ratio is recommended.