I understand what you're trying to accomplish, but personally I wouldn't want to give up space in my living area. There are other ways you could layout your LR furniture so that you could enjoy the view thru the slider and it would save you moving the fireplace and adding another window. I see you have a large window on the left wall and if this is a TV watching area I would hesitate adding more windows. Keep in mind that moving the fireplace would not be a minor expense and I'm not sure adding a jog in the hallway next to the kitchen would be an improvement. How old is 'kiddo' and how much time does he/she spend in the room? Is it possible to set up the 3rd bedroom as a playroom or study instead of trying to make the BR larger? If the ceiling is the main annoyance I suggest you change the ceiling. Have a contractor check out why it's built as it is and see if you can't change the ceiling line to a vaulted one.

NaviJen, pleased to see you posting with us. Mass. is a whole different style of housing than what I'm used to in Alabama. Like lower ceilings, big basements, storm windows, dormers, angled ceilings upstairs. And I've been surprised at the absence of air conditioning (a necessity built into every home in south Alabama), and the intrusive nature of many heating systems--including radiators, baseboard heaters, boilers and oil tanks! Those things take up a lot of space and money to operate also. As older folks who married almost four years ago (second spouses), my DH has a home up there, and I have one down here. That's why I sometimes do a flip-flop from north to south, you will notice. I've been redoing his house AND mine. Jen, be sure to hang in there with us, a lot of creative ideas come from this group of folks. And Steph, you are so unique, giving your boy his own bedroom!!! I'm thinking you need to get out more? hehehehe Having huge antique furniture can be a drawback in a smaller home. Of course, ONE PIECE could fit, maybe, if it is a featured piece. Something that WORKS FOR ITS KEEP. I do hope you have room for the things you've STORED FOR 14 YEARS?!! At least, put it in place and see if it leaves enough breathing room. After all this time, you may have fantasized it into something it can never be, and you've grown out of it....so to speak. Dreams are hard to give up. If I had a good spot to put it, I'd be looking for a nice armoire...just because I like those. But I realize it won't fit my house or my lifestyle any more.

Depends on your skill level. How are experienced are with demo, framing, drywall, spackling, trim work, etc? If you are getting a bank loan it may be against the loan agreements. Your building dept may not allow it as you wioll more than likely need permits and a C of O. As you mention electrical work would need an electrician. Realistically if you need to ask if this would be DIY'able it probably is really not a good idea to attempt.

Here's the WORST thing that could happen. The floor will rip itself apart at the doorways. That's it. That's all. If that happens all you have to do is cut the planks in the doorway, drop in trim, tap the floor back together and off you go. The fun part is: winter is the SHRINKAGE time of the year. That means the summer will see the floor expand as much as 1/2" over a 30ft span. You could see BUCKLING in the summer rather than 'unzipping' along the edges of the plank. It's your call. You have VERY narrow pinch points. That means you need to do ++ door trim (1/2" expansion gap at ALL vertical obstacles = door trim). How good does that look? That big fat 1/2" gap around the door trim?