anyone else regret trying to replace windows themselves?

Haha, reading your post gave me flashbacks to my first DIY window replacement adventure. YouTube makes everything look like a breeze until you're standing there with a crowbar and a confused expression. I remember measuring twice, cutting once, and still ending up with gaps big enough for birds to nest in - true story. Honestly, windows can be deceptively tricky because houses settle over time, and nothing's ever perfectly square.

One thing that helped me was shimming the frames carefully and using expanding foam insulation to fill those pesky gaps. But even then, it took way longer than I expected, and I ended up calling a buddy who knew what he was doing to bail me out halfway through.

Curious though, are you dealing with older wooden frames or newer vinyl ones? Older houses always seem to throw extra curveballs at you...

Haha, I feel your pain - been there myself. But honestly, I think the expanding foam insulation can sometimes cause more headaches than it solves. First time I used it, I underestimated how much that stuff expands... ended up with foam oozing out everywhere and spent hours scraping it off the siding and my hands (pro tip: gloves are your friend).

What I've found works better for me is using backer rod and caulk instead. It's a bit more forgiving if you mess up, and you don't have to worry about accidentally warping the frame if you overdo it with foam. Plus, it's easier to control exactly where you're sealing.

Also, older wooden frames aren't always as bad as people say. Sure, they're rarely square, but at least wood gives you some wiggle room - you can shave or sand down spots that don't quite fit. Vinyl frames are less forgiving; once they're off-size, you're pretty much stuck.

Anyway, DIY window replacement is definitely not for everyone... but hey, at least we get good stories out of it later, right?