Try using a piece of trim a little taller and slightly wider than both of these but with similar shape (rounded at the top). Cut two of them with miter for corner and 90 degrees where they meet the current trim. I would cut these both back at about 1/2." The corner trim pieces would each be about an inch long. The image I attached is to give you an idea even though they are on different levels.

I found an exposes side-angle of the stuff by the stairs. Turns out it's not quarter-round but something else. Has a flat top that the baseboord rests into. I've attached a photo marti8a, yes the whole house it like this. All 2K quare feet. Strangely, inside the closets there's just the baseboard, no wood trim below it. As for the "hammer mark," I think it's just a scuff. There is no indent. snookums2, the flooring is original. The house is only 7 years old and was hardwood throughout from day 1. Any other ideas on why this would be done? Ir is it just a stupid contractor/prior homeowner mistake?

Lazypup - My nails are the same length as my drill bit, so that doesn't help in this situation. You gave me the idea, though, that I could reduce my difficulties by using shorter nails. Would it work to use ones that just only make it into the baseboard by 1/8" or so? Kec01 - I imagine it is oak, since the floors are. It's been painted throughout the house, so I haven't been able to see the grain to say more definitely. (These people! The few things that they didn't cover with wallpaper, they painted over.) I went ahead and finished the room I was working on, with mixed results; I think it did help to pay more attention to hammer technique, but I still ended up puttying some areas of carnage. Since I'm painting rather than staining and ultimately am just not that concerned about the shoe molding, that's an OK outcome. I do think I may try an air nailer once I'm ready to do another few rooms' worth of molding. Will the air nailer have difficulty with the oak? Somewhat relatedly, I'm considering taking the opportunity of the shoe molding being off to spoon some borax into gaps that will then be covered up with shoe, since it is a mild insecticide and this house could stand to have fewer centipedes. This will get it closer to where I presume they hang out, and unavailable to my little kids. Seems like a good idea, but many tales of woe start with "it seemed like a good idea at the time." Any reason not to do this?

I am so glad you like my floors so much! Funny, when first looking at the house, I wasn't sure I liked them. Now I *LOVE* them. Especially after my DH sealed them with a high gloss finish. YUM! No, you don't see anything between the wall and the ceiling, although I can see where you can't really tell what the heck is going on between the wall and ceiling. One reason I am really considering crown is the guys who did the knockdown on the ceiling...they did not make a *clean* cut between the ceiling and the wall. It is not noticeable in the dining/living room or the family room because the walls are painted a sandy white (and we plan on picking a more exciting color eventually, we are just overwhelmed right now and played it safe with the off white...but do you like that wall color? DH said maybe we should stick with it, because we want our floors to stand out...we don't want wall color to compete w/the floors. This is a topic for another thread, probably, LOL.)but in our bedroom, which is painted a dark, army green color...it is very noticeable. Also, my DD's room is painted a deep red. The line between the wall and ceiling is not "crisp." Can I do crown in only the bedrooms? Is that weird or acceptable? Also, in DD's room, I am thinking of getting funky and doing a black crown, even though that breaks the "rules." Her floor is a "Sambuca" colored bamboo...it is almost black. Her baseboard is the same as the rest of the house...almost 5" off white. Anyway, thanks for the continued help and support! I am very overwhelmed in this house, it is such a blank canvas which sucks when you are a) a decorating novice and b) on a tight budget! :(