Anyone can do it Lisa. If you need a header transition on the right side you would square it and install the header with the groove facing out. If the header is on your left, install it with the tongue facing out. When you get to the headers start your rows off the headers, working right to left or vice-versa. Sometimes there will two header transitions opposite from each other and you would need a router. I'm in SW Virginia homebound. I use a piece of MDF to create a template and place the template down on the flooring and then cut the radius using a router.

Using a diamond blade, one could cut a diagonal line across the tile, either at the end of that handrail or somewhere between the handrail end and the start of the curve and remove a small portion of tile. This would tie the big room upper left to the small area lower right in your picture and you could use standard transition moldings. As to your tile grout issue, you might look into whether you could hire someone to clean and seal the grout or remove it and regrout it. Everything has it's drawbacks including wood. While it doesn't have grout and isn't prone to fracture cracks, it's more sensitive to water, humidity changes, dings and scratches. It should be recoated periodically. High wear areas will need recoating before low traffic areas. On the plus side, many wood floors can be refinished and you can change the color, unlike that pink tile someone thought looked great 15 years ago.

Thanks for all the thoughts. Sounds like tile on slab would be firmer on feet than wood on slab. I'll also look into the Marmoleum Click suggestion. Have to admit I'm a bit of a snob on the idea of vinyl but I should look at it. Thanks for the shoe suggestion! I have a chronic plantar fascitis problem and have been fighting peroneal tendonitis for over 2 years. I am always in either my Birkenstocks (use for house shoes/slippers) or sneakers with custom orthotics. Every step. I miss being barefoot -- was a total barefoot person before. On transitions my concern if I go with wood is it would be an big opening from the kitchen to the LR/DR which has a wood floor that I cannot continue there (rustic boards nailed in - I don't think it can be matched on the slab and it has gaps that I don't love for the kitchen (have it in my kitchen now). So I'm not sure how it would look to have a big wide opening changing woods. Like the tile examples above I guess some boards placed across the opening framing the transition point.

Do NOT do that.. Put the wood on all the floor, including kitchen , and use the tile on a backsplash. You are already too close to the sink wall with the island. move it out six inches. Opening the dishwasher is going to be incredibly inconvenient. Shrink the island to four feet. It appears a kitchen that perhaps should not have had an island at all. One where a peninsula may have been better. Hard to say from the limited sketch. No matter what, the space is too small to be cut up with two different floors, no matter the selections.