I learned that the cheap "builder grade" windows that came with newer homes (mine was built in 2005) are pretty subpar compared to quality replacements. They started failing (foggy glass, broken balances) in barely 15 years. The new ones I got are worlds better. So even newer homes can benefit from an upgrade sooner than you think.
One thing I insisted on after reading up was that the installers use insulating foam around the window gaps (not just caulk). They did, and I think it helped eliminate drafts. Make sure whoever you hire pays attention to insulation in the install process.
Big kudos to local family-run businesses. I went with a smaller company (not one of the big names) but they had stellar reviews. The owner was involved from start to finish. Sometimes the little guys really care and it shows in the result.
Before signing, I checked my contractor’s license on the Florida DBPR site and also their insurance. Gave me peace of mind that everything was legit. It's tedious but worth it.
Echoing the HOA experiences: our HOA didn't outright restrict windows, but they required we submit the product brochure and color sample for approval. It added about 3 weeks of wait before we could even order. So definitely loop them in early if you have one.
The permit fees in Hillsborough County for my window job were about $200, which my contractor handled. It was itemized in the quote. Not huge in the grand scheme, but good to know it's part of the cost.
After installation, our stucco patches needed to cure before painting (as @poet45 mentioned). We walked around with a tube of matching caulk and some paint and made those new windows blend right in. Just budget a little time for the finishing touches.
One surprise: the hammering of installation caused a tiny crack in my bathroom tile near a window sill. It was an easy fix with some filler, but heads up that the vibrations can cause minor cosmetic cracks if things are brittle (like old tile or plaster).
We opted to do our own interior trim to save a bit. The installer left the inside sheetrock around the windows exposed (which was agreed on). I spent a weekend installing wood trim and repainting. Turned out nice, but if you're not into DIY, let the pros handle the finishing. I have new respect for trim carpenters now 😅.
I came here looking for tips and I’m not disappointed – this thread is amazing. Keep the insights coming!