Don. Be sure to compare the backside of the dampers. There is an un-balanced damper that has one of the three 'spokes' that is thicker than the other two. Be sure your old and new look the same.
Many years ago, I reolaced the timing chain on my 91 4.3 DD pick-up I had just purchased. I have removed the timing cover on numerous small-blocks, without removing the pan. I trim the upper, inside, ends of the 'chanel' that the front seal goes into, and it's possible to 'tilt' the front cover back onto the block, with no leaks, problems, etc without touching the pan.
On the 4.3, with the one-piece pan gasket, I messed around for an hour or so, until I determined that the above method was NOT going to work. I did not want to remove the pan. I cut the pan seal on each side, and put it in the timing cover channel. Some RTV in the logical places, and it went in like a small-block. No fuss at all.
When I retired this engine about 8 years and 125K miles later, the 'repair' area was still dry.
Moral of story: Don't be shy about removing the cover, checking the chain, and installing the seal in the cover on the bench.
Hint #2: I use a propane torch on the damper hub to expand it prior to installation. It doesn't have to be real hot, for it to be loose enough to put on with only a few light hammer taps. I've been doing this for years. I've had a couple get too hot, ie they go on too easy, and worried about heat-damage to the seal, but it's never happened. Works with crankshaft timing gears also.
Regards,
Dave.
PS I'll be interested to hear how far off the NEW damper timing mark is. I don't think your old one slipped at all.