Not sure if it’s too late to chime in here but as a new homeowner who also knew nothing about windows, figured I’d share what I learned:

About Anderson windows: we have 3 old Anderson wood windows in our bay window area. To their credit, they are 30-something years old and still function ok (compared to the old vinyl windows throughout the house that we have been slowly replacing). However, to their detriment, they are hard to service in our area; one of ours is cracked and I think we are better off replacing it entirely versus just getting the cracked panel removed. The reason I say it’s better to replace is because these windows are already pretty drafty, which leads to my next point.

Someone previously commented about vinyl windows and, based on my research and what I learned from various vendors, it’s a great cost effective option because (a) they are reasonably priced and often have good warranties and (b) the vinyl frames are full of insulation so they are more energy efficient.

We ended up finding a vendor in our area that sells Okna windows but we weren’t particularly looking for that brand (we told them our needs, and they came back with that suggestion). We went with a Deluxe mid-range option that cost us something in the neighborhood of $400-$500 per window (including carting away of old window and installation of new). Most of these windows include screens which is super helpful if you hate bugs like I do.

So far, we are happy with the new windows. Our master bedroom had 2 really terrible drafty windows and the new ones make a tremendous difference in our comfort (keeps in the warmth generated by our old cast iron radiator). There’s also a bit of a dampening on outside sounds as well with the more energy efficient windows.

As for dealing with vendors, it might be good to assess what you have and the reason why you are replacing — is it for style? Or is it because the windows don’t function (won’t stay open, fall out when opened for cleaning, etc)? For us, the reason for replacing was more so the latter and so when we discussed with vendors we emphasized longevity and matching the style of the existing windows, while also reaping the energy savings of new products. Good luck!