I would extend/match the hardwood into the entry and hallway, stopping at the kitchen. Then when you're ready to re-do the kitchen, you can find the appropriate tile or other flooring that will go with whatever changes you're making.

Hi, Mikey--

Congrats on the new buy! Are you folks planning to keep the chair rail intact? It's in some of your photos, but looks like it's missing from the picture near the entry door. Just trying to get a feel for how much molding you're planning to end up with. Agree with @Sabrina that weaving in the hardwood would be the plus here. And your demo team would be able to remove the existing thinset and backerboard under your cracking tile to get your wood flooring install level.

I'd also recommend painting your stair risers and skirtboards in your existing trim white to cut down a bit on the amount of wood happening in your stair build as a part of your planned paintwork.

I agree that continuing the wood throughout would look great. A professional installer can work magic.

the tile and the wood can be the same. if that wood is solid, it might be thicker than the tile.

In any case, total demo of the tile and scraping every last bit of thinset will need to be done to lay wood. if it needs to be raised, then an overlay can be poured, or a thicker subfloor can be screwed down. not a big deal.

question is, can you match that wood? is the current floor red oak, solid? engineered? can you match it? if so, do that.

if not, pick a porcelain tile that you would like to carry into your kitchen.

a natural black slate

or a 24x24 porcelain tile

if you want to do a large hex, this would be a way to get rid of that horrible transition piece,,,or just use a metal edging piece to span the change.

Just came here to say I really like your front door!