Yeah, so, I totally feel you. I have a big soft spot for houses, and I own a lovely old drafty impractical thing that is too big and costs way too much to heat, and they're going to drag me out of it feet first.
I think it is reasonable to buy a house that fits your needs and makes your life easier, as long as you do the math and accept the tradeoffs. Yes, you make do for a while, you try free/cheap options to see if you can make it work, but if you are still dissatisfied about fundamental things that you cannot realistically change (like, say, location), it is reasonable to look to move.
The problem is that it's really hard to separate that sort of logical analysis from basic house lust. I admit, I have had house lust several times -- the most powerful one when they built some new houses in the "right" school district (as we are in the "wrong" one), and the thought of open spaces and functional insulation was pretty powerful. But is it a real need, or a real want, or just a daydream? The way I tell the difference is to mentally imagine myself in that situation -- not just "wow wouldn't this kitchen be great," but how it would feel to pay the bigger mortgage (at a higher interest rate), whether I am going to be happy 10 years from now when I am going to work for X more years knowing that I am doing it for the house, how it will feel to pack up my stuff and to say goodbye to this place forever. For me, all of those thoughts completely nauseated me, which told me that the spanky new house wasn't worth the extra money.
Why don't you do some real research? Instead of just drooling online, research real costs in that area (home prices/taxes/insurance, plus higher utility usage/maintenance/etc. with a bigger house), look at current mortgage rates, how much you'd have to put down, what your selling costs would be; think about what will be closer AND farther, because everything has tradeoffs. Think about how much longer you'd need to work to afford the new place, and then start looking at houses in that price range -- can you afford a house that will actually make your life better, or in your price range would you just be replacing one set of problems with another?