chipped latex over oil...help please

Hi

I am trying to paint nearly every square inch of my 80 year old house to get it ready to sell (hopefully by next weekend as time is passing me by here so I only have a couple of days to get finished). Anyway, where some ne'er-do-well painted some of the original wood trim in oil (I wish they had just left it alone in all it's glory), someone else seems to have covered it with latex. Then someone else put that plastic insulating stuff up which left tape residue and when they removed the tape, they pulled paint with it. They also painted latex over the shellac on a door and it's all cracking too, so same issue there.

It didn't really bother me when I purchased since I had time to deal with it properly but such is life, it didn't happen. Now I have to deal with it and have no time for stripping it all properly. It won't all just scrape off either and even sanding doesn't get the edges down enough because of the detail in the trim (I would guess there are 3 coats of paint on top of the stuff that is letting go).

What would you suggest I do? I could just break out the Zinsser and prime and paint it all, lumps and bumps and all I suppose but I'd rather try and get it even somehow. What I don't have is a lot of time to do a lot of work and even at the risk of having someone in the future swearing at me the way I'm swearing at whoever did this, I really don't care right now. I just want it looking reasonably decent to sell.

Also, in one room the quarter round has separated from the baseboard. I was just going to nail it back but realized some idiot glued it to the wood floor. So I have a space running from flush to at least 3/8" away from the baseboard between the corners. What can I use to fill that space before I paint that trim? It seems a bit big for caulking.

Jean