I have the same problem (new floors will be lower than old carpeted floors and I'm planning to re-use the same baseboards after I paint them). I am trying to do what was recommended here from 11 years ago to get rid of the line and retexture the "Below the belt" area since the baseboards will sit lower. However, I realize this is going to take me weeks by myself and I'll have to finish it up after the guys have installed the new floors, which means I risk messing up my new floors and/or doing all the draping and cleaning that I dread. Sooo... Can I have the floor guys add a piece of trim below my old trim like a shoe edge or quarter round (although i hate the way a quarter round looks). Is there something that anyone would recommend that would not look hideous. Here are photos of the existing trim with my old carpet and a picture of another wall after the carpet and trim were removed. The style of our home is nothing spectacular. It's a basic 90's ranch that we're updating.

A wide putty knife or a long drywall mudding knife and a reciprocating saw with a long metal cutting blade. Slide the knife between the baseboard and wall. Using the recip. saw at about a 30 degree angle, find the height to position the saw so the end of the blade just misses hitting the floor. Then pull the blade until you feel a nail. Cut the nail and proceed until all the nails are cut. You can then use the knife laid on the floor as a guard to pry up the base molding. The other option is to rent a jamb saw and simply cut all the molding flush with the floor. You can then simply install new base and shoe moldings.

This is what most people use, as far as I'm aware. Get the "Flush cut saw blade" at the bottom of the page. If you are really good with a saw, you might be able do it with a Japanese-style saw. Here is a link that might be useful: FMM

It's normal for a person who has never removed a baseboard before, and was not aware of the procedure HandyMac described ( did it myself once - but only once!). Since you have two similar holes caused by the prybar, then you not only are dealing with no experience, but no interest in learning from their mistakes, and no thought to preventing damage to your home. I would be quite concerned about the quality of a floor install, if this person is on the crew! I would expect the flooring company to be responsible for repairing the wall - but I would not trust them to do it themselves. For the repair to be virtually invisible, it needs to be done by someone who knows what they are doing. Hopefully your flooring contractor agrees with you, and either hires someone, or provides you with enough of a discount to cover the cost of you hiring someone (or fixing it yourself, if you are so inclined).