I’d get more quotes. That is a crazy price for a few hundred SF of new flooring and refinishing existing unless total SF is huge. The last thing I would do is an ‘almost but not quite’ match of hardwood- tile is way better choice than that. Another thing you could consider is to do same oak flooring finished to match existing but separated by a contrasting inlay so you don’t have to refinish all the rest of the flooring.

My only debate with a lower sheen is that our has has very few windows. We have a large sunroom which is great but we’ve come to find that the rest of the house isn’t so bright and really only the kitchen window and one of the bedrooms gets direct sun shining through so I’m worried a less sheen will look dull. I may ask him to do the first coat semi gloss and if it really is too glossy I’ll switch to the satin. Did you go with Loba or bona matte?

I like the color you have! It is classic. Maybe not "on trend", but it won't be the gray floor of 2017 for the next 40 years either. Anything "Medium Brown" will be classic. Achieving that on red oak is not always easy due to the red part of red oak. Seriously, though, there is no easy answer to this without samples on your floor in your lighting. You can't make your decision based on pictures on the internet because of the variations in lighting and whatever your monitor does to colors, too. If you can't slow the process down to get samples, I would make my own samples by getting some unfinished red oak and staining it yourself. Be sure to add the top coat to get a realistic idea of what it will look like. Then you can move the samples around. However, you need to know what brand of products your flooring professional is going to use. If you have that information already, please share it and the professionals here will be able to give you some input on the quality of the product.

IMO outlets are never design features and I really dislike floor outlets since they now drive where you can put furniture always. I do not see any in the pic so maybe a better pic of what you have now. I usually use cable lighting for this type of style since it lends itself to very contemporay spaces.