Those pegged wood floors have great character and that LR has so much potential. I can't wait to see the transformation so I hope you share pics of the progress. The bedrooms look a little small so I could see how wood flooring could help to make them feel more interesting and spacious. That last photo in particular really shows that dark trim you were talking about and, if it were me, I'd have a really hard time not ripping that out and replacing it with something nicer in white. It might look fine just left in place and painted but someone would have to do a Photoshop mock-up for me to visualize it.

I would think they could use the woodworking technique of “coping” (basically undercutting the molding). Have them Google the term or look at a YouTube video.

Wow thank you both so much for your insights! I did not know maple Is so hard to stain! Does painting maple still have the same outcome as staining it? I chose maple because my contractor said that would be a more durable choice :/ my vinyl is shaw floorte vinyl and it snaps together. if I chose to do vinyl on the stairs my my guess is I could glue it to the maple stairs? sorry for all of the questions but know that your help is very appreciated! I am new to this! Thank you

Elephant in the Room: "...we are having a friend do the install..." This is fine with flooring (as in hallways, bedrooms, etc) but not a great idea with stairs. As everyone has said (and I will repeat myself) stairs are EXPENSIVE because they deal with CODE. A 'friend' will have to be willing to take ALL LEGAL RESPONSIBILITY should the product that s/he applies cause A. injury or B. fail code. Most friends aren't that excited to be on the hook for 'helping out'. Carpets HIDE the WORST MATERIALS in the building world. By worst I mean CHEAP and POORLY made. That NORMALLY includes OSB. OSB can be the cheapest of the cheap. It is made up of 'chips' of wood glued together with a waxy substance. The very make up of OSB PREVENTS stuff from being GLUED to the surface. Enter: Vinyl stair covering. Vinyl planks/nosing MUST BE GLUED to the stair's substrate. Imagine the substrate as the WORST OSB possible. Stairs need to be strong and meet minimum code. Builders LOVE to use the CHEAPEST MATERIALS on stairs because stairs are INHERENTLY expensive. So....save $300 on the stairs and you have $300 in your pocket (the GC/Builder). So long as stairs are DESIGNED to be carpeted the architect and builder have NO INCENTIVE to make it out of anything other than OSB. I know this is all new to you. So I will spell this out for you: your assumption about plywood (plywood is EXPENSIVE = saved for places where it is NEEDED) is, sadly, a problem. A plywood stair would be AWESOME for your situation. But I would bet dollars to doughnuts you have OSB. And the subfloor UPSTAIRS is probably going to be OSB as well (see discussion about costs of plywood). OSB does VERY WELL under carpet. Carpet can cover hills and valleys and sagging sections of the subfloor (OSB does ALL of those things and MORE). As soon as you want to put down a rigid floor (where carpet used to be) you MUST ASSUME a LOT of patch/repair. Again, this is where the COST of the repair comes in. I have told my clients to BUDGET $2-$4/sf worth of SUBFLOOR REPAIR when removing carpet. Yes. That is the same price as the vinyl planks themselves. The subfloor repair can DOUBLE the cost of your project. Now ask your friend if s/he is GOING to do the 8-16 hours worth of work to PROPERLY prepare the subfloor upstairs. This is when using a friend gets tricky. So long as you are paying them FULL MARKET VALUE for their labour/skills, your friendship will remain solid. If they are doing this for beer and pizza, then things are going to get VERY tense. I know this is new to you, so be PREPARED for MUCH BIGGER project costs than you originally anticipated. If you have to repair the upstairs subfloor AND REBUILD (remove the OSB and then lay down NEW PLYWOOD on) the stairs you are in for a MASSIVE bill. Rebuilding stairs is worth the same price of the vinyl AND the cost of labour to repair the upstairs subfloor. It runs in the THOUSANDS of dollars. Just so you know.