What kind Of Interface? Or A Tale of Two Leaks

After Yesterday's cold front passed and the rain moved on we have a cool, clear blue sky morning.
We are living in a house that we bought at foreclosure. It needed a lot of work but I'm pretty handy and the price was CHEAP. The two main concerns with a house that needs a lot of work are the foundation and the roof. Both are big money items that can cause a large dent in the account. With the exception of a small place on the roof both items appeared good. We had several rains last spring and summer and they revealed a roof leak that terminated in the houses entry. Great. We spent quite a while chasing the leak and finally found a roof vent that had a really crappy installation. Last Sunday I pulled some shingles off, tore out the roof vent, replaced some roof decking, installed a new roof vent and re-shingled the area. Good to go. Last night the rains moved in, light sprinkles followed by a drizzle of several hours. The repairs I made proved rain tight, however, the rain revealed other leaks. Now we had several rains earlier in the year and these places showed up but we applied some roofing tar to the roof/chimney interface (how do you like that phrase) and that leak stopped. So last night the rci started leaking again. Like it has never done before. Towels, buckets and tubs were all employed in catching the intruding rain water. So, here we are in the first week of November. There won't be many good roofing days to come. So, the first warm day we have, I'm climbing back up on the roof with a 5 gallon bucket of sealant and plastering the living shit out of the that damn thing. If that gets us through the winter( remember that song " If We Make It Through December") I'll tear off everything around the chimney and start fresh. Oh, to add fuel to my internal fire, after my ride yesterday morning I found that the base gaskets supplied with the cylinders I installed on my Harley are CRAP. So this winter I get to remove the top end of the motor and install new base gaskets. A blown base gasket is what started this whole rebuild in the first place. Of course, I wasn't in the best of moods last night, but we have a whole new day before us.