I'm rehabing a portion of my house and could use some advice. I either need to find a good way to transition hardwood to ceramic tile -or- find a way to match some new hardwood to my existing hardwood.

First, how difficult is it to match new hardwood to old? The existing is 50 year old oak. I've already refinished my living room and didn't use any stain. If I can't match, how bad would it look to have my kitchen or both kitchen and dining room be off color from the rest of the house? Does anyone else have this situation in their house?

Second, I've seen people mention making sure a tile floor is level with hardwood, and then using caulk to fill the gap between. Does anyone have a large transition done this way and does it look good? In my design, there will be chairs at my island that, when pushed back so a person can get out, will cross the transition. Is that safe or will the caulk and edges catch the chair leg?

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Thanks

Justin