I figured id kill a few birds with one stone instead of posting 3 seperate threads

My first issue that im mainly concerned with is my windows, only the front two.
Ive heard that MK4 Jetta's have some problems with these and I think I am to. When I push for it to go down it goes up and vice versa. Its annoying!! How much would this cost me, roughly? I took it to SCFC and they said it was just stuck cause it wouldnt go down at all so they "lubbed" it.
Second, My passenger side headlight keeps going out. I replaced the bulb like 3 months ago and it burnt out this morning. Why is it not lasting the way it should be?
Lastly, the tail lights, I put in some aftermarket tail lights. Even before this I had a slight leak in my trunk. About a month ago I took it to SCFC and they balmed it on the aftermarket tail lights and said they would not fix it. So Im going to fix it myself. How would I go about sealing the small cracks between the lights abd the body?