Looks fairly rustic, you could just use a piece of square stock in lieu of shoe moulding.

@millworkman - are you suggesting a tiny piece that just fills the gap, versus on top of the baseboard? Here’s a picture a bit farther back… as you can see, there’s a consistent 1/8” or so gap everywhere - that doesn’t bother me because it’s actually under the baseboard (we could pull off the baseboard & re-install it lower, but where the register is actually a tiny bit smaller it would still show that ugly jury-rigged fix..)

@jrb451 - that may work - especially if we were to re-install the baseboard a bit lower!

No I am saying using square stock in the exact same manner you would normally use a shoe or floor moulding, quarter round is not an acceptable substitute in my opinion.

We used doorstop molding because we didn’t like quarter round.

Thanks @ker9 - trying to stay away from any kind of molding, because we’d have to use it at the very least on the entire wall (25’) where the buggered up register is

@shadywillowfarm - ah… yes, just realized we’d have to move the baseboard down in the entire space to get it right. We just had the whole house painted, so the paint would match fine, but I don’t think I’m up for moving that much baseboard…thanks for getting me to consider that line of thought!

@millworkman - I 100% agree on quarter round not being acceptable - it looks just like what it is - someone goofed somewhere and now is trying to hide it (LOL in this case, there WAS a goof and that’s exactly what happened!) The square stock might be a great alternative, as it would certainly fit in with all our straight lines better!

With all those random colors going on what's wrong with neatly caulking then fill in colors with artist's brush?

@klem1 - yea, that’s probably what we’ll do - I think that is what the previous owner tried to do (poorly, then covered it up with 3/4 round). We’ll try living with it for a bit longer and see just how much it bugs us!

Caulk comes in a variety of colors, why not just try a bronze color caulk?

There's a quite simple fix. Remove the existing baseboard, purchase new, scribe to the floor and install. If you make the new base slightly taller it will come above the live where the current base meets the painted wall.

FYI, SHOEMOLD is narrower than it is tall, where quarter round is the same width and height, like a quarter of a round. A properly finished shoemold would just about disappear against that baseboard. For an even more minimal option, one could take doorstop material and rip it down but it may be a challenge to find it on decent wood so it can be stained to match.

If you have straight enough floors that you could install it right on the floor, I would buy all new taller baseboard, an move it all down to the floor. Be aware, you will need to scribe some spots where the floor is higher or lower. When you remove the old, there will be a thick line of paint, and it will all require a lot of work, to get it to match the newly painted walls, so I definitely would not try to move the old down.

Thanks @Timothy Winzell and @cat_ky… we may consider moving the baseboard down - that would be a big project for sure, since it’s about 50 ft of baseboard that spans both the family room and flows into the kitchen (then the caulking/painting)… Sure is annoying when people just don’t do the job right the first time…. Sure appreciate all the great suggestions!!

I don't want to offend you but it seem's you are un-nessarrily obsessed with this and if you aren't carful the fix may turn out worse than when it began. At the onset you said "as you can see, there’s a consistent 1/8” or so gap everywhere - that doesn’t bother me because it’s actually under the baseboard but where the register is actually a tiny bit smaller".

I agree the messy caulk between vent and baseboard look's awful but is simple enough to fix. Since the other 50' of baseboard doesn't bother you,either install shoe mold or leave it alone. Scribing baseboard to uneven floor is so unreasonably difficult I've never seen pros skip molding in favor of doing it.

I suspect that there is no flooring on the back edge of the vent. So someone caulked in a sorry attempt to hide a bit of visible subfloor.

IMO, scribing the base to the floor isn't all that difficult. But it can be time consuming. It is faster & easier & cheaper for the pros to just slap some shoe mould down vs the cost of labor to scribe the base. (Back bevel the bottom of the base if it appears there is quite a bit of material that needs to be removed.)

I would remove the base & set it lower. Touch up the wall paint before reinstalling. And fill in the floor behind the vent if what I suspect is happening re: the caulk...if it is going to show when the base is set lower.

@klem1 - no offense taken - not particularly obsessed with this - I was just looking to see if there was a “quick” fix for this - and you all have given me lots of great ideas - including just leave it be :)