Well you are reaffirming what I thought in the first place. Glad to hear there's potential for it not to be as messy as I recall from the last time I did this. Part of my problem is that I'm just not up for moving everything again after only a year which of course I'd have to do no matter what I replace the carpet with. The stairs are the worst so I think I'll deal them first - no furniture moving required and they can pre finish before installing with just some final touch up. Planning to add some kind of patterned runner that doesn't show dirt and wear. I guess I'll focus on that project for now.

Some might scoff at real stuff next to fake, but I have a few areas of real next to fake in my home which look fine (stucco next to hardie board, real marble next to fake ceramic marble tiles, and wood tile next to real wood to name a few). My wood next to wood tile is running the opposite way and I think it looks fine and was a good tradeoff considering the functional improvement tile provides in combined kitchen/mudroom area and the difficulty of matching 100 year old douglas fir, however 1) The opposite direction run makes sense for the orientation of my kitchen, that is the tile runs with the long dimension of the kitchen 2) Its at natural room transitions, not an abrupt change in an open room 3) The two woods are clearly different from one another so not trying to "match" per se and missing but they are in the same tone family, that is (to my eye at least) both are a neutral brown without any significant grey/red/etc. 4) I carefully picked a tile with some texture to look similar to the 100+ year old original floors. In your case, I'm not sure it works so well. Seems like you have grey "wood" joining with the actual reddish wood in what seems to be an open(ish) area. Also one is sort of a distressed rustic sort of look whereas the other is a shiny smooth (I assume prefinished) look. Seems like you already bought your tile, not sure if you have the opportunity to still change your mind. If you are 100% committed to the floor, I'd do them opposite directions.

Watch out for vinyl...it normally doesn't like in-floor radiant heat. Then again neither does wood (engineered hardwood can be used...but it must be SPECIFICALLY designed for in-floor radiant heat). Cork is out. Carpet is in. Concrete is in. Tile is in. Stone is in. Linoleum is out (doesn't like heat). A concrete floor should cost around $7-$18/sf...depending on what you do with the colour. A fully functional clear epoxy coating (with the appropriate aggregate used) is $7/sf. If you want to add colour you can climb the ladder very quickly into the $18/sf range. A STUNNING 'artistic' stained concrete floor with 3+ colours = $18-$25/sf. That includes the coat of clear epoxy. Be aware of concrete's maintenance needs. It is a high-maintenance floor if you do it 'on the cheap'. You can grind concrete and then polish...that's nice but you still need to pay for the proper micro-topping. That's the base floor for $5/sf. It stains. It etches. It is a dusty headache. If you 'seal it' with a wax like application (add another $1/sf) you need to reapply the wax every 6-12months...for ever. If you seal it with urethane (low end finish) you need to reseal it every 2 years...forever. You can seal it AND add wax every 4-6 months. But you have to keep doing that for a LONG time. And then every 5th application you need to strip the floors and start all over again. Clear epoxy is your toughest finish that still keeps the look of 'concrete'. It does not need maintenance. But the price tag starts to go up quickly. And you still need the expensive finishing concrete we call a 'microtopping'. If you are looking for economical...concrete probably isn't you best bet. Carpet is better bang for your buck.

If you insist on the lighter flooring, then I would go with the slightly darker version (the one on the left in the last photo). Are you keeping the brick? If you are, the slightly darker wood floors are a better compliment than the super light wood. If you are removing the brick and rebuilding the stairs, then you will want to find out if either of the vinyl floors have stair treads and nosing available. People who have used vinyl that does NOT have treads/nosing found their BIGGEST headache comes from trying to find a solution to this problem. As for your darker wood floors, they look (just one photo with one chip out of the wood) like they could be ready for a sand/refinish. If they are, I HIGHLY recommend doing the hardwood FIRST...and then choosing the fake-wood look product for the den. You might find a good colour match can be had if your red oak hardwoods can be sanded and refinished as 'raw' = the colour of the planks you want to use. How old are your hardwood floors? If the finish is very close to 20 years old, they are ready for a full sand/refinish. It is always advisable to figure out the BIG ticket item before you try to figure out a small ticket item. And if you are refinishing the hardwood, why not add more of the same??