I would say all of the pricing is appropriate. You’re always going to pay a premium for a small job like that, because the contractor could be making double or triple on a job with more windows. That being said, if the only difference is “insulation” between the first and other two vinyl options, then $200+ is a lot to pay for what I suspect is actually “foam” in the chambers of the vinyl extrusion. All four bids should include insulation around the outside perimeter of the window frame between the studs. However, there may be more to consider in assessing value — frame depth, cosmetics, fold-away hardware, warranty, installation company, etc. Again, none of the prices strike me as unexpectedly high for what you’re looking to have done.

Thanks for the input.

I'm still hesitant to hire someone to do this work. I read something about a brickmold technique. Basically cut the metal siding with a circular saw and using the J-channel as a guide. Using the narrow side of the saw will set the spacing just right to expose the existing nail strip to remove the window. Then if you get a window wit a brickmold, it will cover up the new nail strip and still allow room for j-channel. Have you ever done an install like that?

Haven’t done it that way before. Dealing with aluminum siding and the exterior envelope isn’t the place to try something new. Your hesitant to do the work yourself. Your hesitant to pay someone to do it. You might as well pay someone to do it that’s done it thousands of times rather than pay someone to take care of a leak you did yourself. You may be plenty capable, but if you felt comfortable doing it yourself I don’t think you would have gotten four estimates.

Those numbers are a single estimate with 4 different grades/lines of windows.

Ok. So install should be the same. If it’s 4 options from the same contractor, that makes me think the cheapest one is that much cheaper for a reason that will make you regret the savings down the road. What are the 4 brands/lines quoted?

Windows by Unlimited (made here in WI) was the cheapest, soft-lite were the middle 2 and Marvin inifinity was the highest.

Marvin Infinity includes install through authorized companies. . . . Get a quote from a different couple guys and include Marvin Integrity fiberglass as one option. That version is available to buy without installation. Fiberglass beats vinyl. Keep researching the install. And consult Marvin's installation instructions. You should be able to do this yourself and get a better window for less. No hurry.