What home improvement work did you do today?

Going through the ceiling would be a lot easier but if the ceiling is finished,yeah that would suck ,patching, mudding sanding and painting the whole ceiling.
But it will be a solid connection, so the other way around it would be an angled boot,if you can finagle it into place this will be your cheat, for the ends that butt up together you'd need to put FSK tape on the 4" crimp throw to help stop any leakage after that nonsense, toe nail the top flange to the sub flooring with Zip screws (pre drill holes in the lip) to save your sanity.
From my years I'd go through the basement ceiling, you won't be any happier doing the "hack and butch" route.

 

That's a sweet looking table,looks thick and solid I would guess the ends are the extensions?
That's a nice set or sure.

 

It says it weighs 250 lbs assembled and I believe it! It's definitely not a high quality solid hardwood construction but at least is all wood of some sort with no laminated fiberboard. The ends you see here are just the ends of the standard length - there are hinges at the end so it'll fold out to add another almost 3 feet!

 

Added a 12x14 shed with double lofts.

 

Made some 5’ tall shutters. 4 more to go.