I think you need to strip the stairs down to bare wood and then compare some samples of the flooring stains to to get a close match with the 2 different woods. You need to find a good flooring finisher not your contractor.

Having two separate floors does not requires having a matching flooring, a lot of people choose different floors for upstairs nothing wrong with it.

I'm not sure what LVT is. :) I have an appointment with the flooring person for Saturday to test out samples. Cherie, we hate forced hot air because it bothers my and the kids' asthma and allergies so I am actually very happy about these baseboard radiators as radiant heat is much easier on the lungs since it's not blowing hot air all over the place. There is central air for the summer months. We live in Northern NH... it gets cold here for sure. I am going to keep the tile in the kitchen for now and the rest will be new flooring *all going in the same direction* ! We are ripping out the red carpeting, which is in all four bedrooms as well as on the stairs. We want to replace that with flooring and we don't want yet another type of flooring in the house so it makes sense to do the living and dining room as well. When we reconfigure the kitchen, we'll have to match it up and remove the tile at that time.

Make things you walk on one finish and things you walk through another finish, it will help to alleviate any confusion if such issue arrises. The trim acts as a frame to present doors and windows and such and should have some continuity in the interior design of the home.