More Vinyl Window replacement

I am going to replace some windows (leaving the frames), and am looking for your collective wisdom.
Mine are 50's era double-hung type (I doubt the era is important).
The way I plan to remove/replace them is from outside - remove the wood trim which retains them; pop them out; pop in the new ones and secure with some more wood (quarter round I 'spose)/ Caulk and paint.
Seems fool-proof, right? Any tricks or gotchas I should know? Or other comments?
Thanks
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Steve wrote:

ground. I did it from the inside, removed the stops, dropped out the old double hung, removed the weights and sash cords (you can just cut the cord and let the weights drop inside the frame.
Then I measured the inside of the opening, top and sides. I suggest you measure at least 6 times using different areas to use the smallest opening. Then I ordered single hung, double pane vinyl windows, dropped them right in, shimmed and caulked where needed, replaced the stops and that's it. Did 3 windows in about 1 1/2 days. It was really easy once I got started.
Hmmm, now that I reread your post it looks like you might be replacing wood with wood? Don't know about that situation.
One thing, my house is over 70 years old and its amazing how well they were built.
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I just replaced 5 windows (no sashes) two weeks ago. 5 windows took about 2.5 hours. I had to widen the gap between inside sill and outside trip (didn't want to remove the outisde trim as it was secure and in good condition. I measured the windows, ordered to fit (use smallest measurements for each window). All you have to do once the window is prepped if you keep the outside trim is place window in the opening, shim for square and plumb, screw window to from, add insulation to gaps, and seal with inside trim. Very easy! Contractor estimates were around $3,000. Did everything myself for about $600. I did all of the work from the inside. I caulked the windows on the outside by opening the window and leaning out.
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The vast majority of the houses built in any era are and were crap. The ones that survive long enough to be houses from another era mostly aren't.
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I have put in more replacements than I can remember and have found it much easier to do from the inside. If you are careful removing the stop it will go right back on. No need to buy/cut/paint any new wood. It is easier working from a floor than from a ladder especially when removing and stuffing the old weight wells. Cleanup is easier, with a piece of plastic on the floor, than picking nails,sash cords, weights, etc out of the shrubs and grass.
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Without correct flashing which requires removing siding, you are wasting money.

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i agee with doin it from the inside . i suggest you get the low e glass.it really makes a difference.
http://www.minibite.com/america/malone.htm
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This is to inform home owners interested in purchasing replacement home windows about one couple's experience with a Northern Virginia firm, CONSUMER CONSTRUCTION, INC.
In June 1999, Consumer Construction, Inc., Woodbridge, VA 22191, 703-491-0745, http://www.consumerconstruction.com, furnished and installed 13 ea. replacement vinyl windows, Carefree brand, with Low E glass and argon gas. Cost: $4,200.
Initially my wife Robin and I were generally pleased with the product, however one double-hung unit toally filmed over within three years on the inner (sealed) surfaces. Those surfaces cannot be cleaned.
We left several phone messages with Consumer Construction, Inc. (hereinafter called the "company') but received no response. In June 2004, we sent the company an e-mail mesage via its e-mail response line. A male from the company phoned and agreed to inspect the window, but never showed up.
We subsequently contacted the Better Business Bureau (BBB) of Greater Washington, D.C. (202-393-8000, www.mybbb.org), which made contact with the company. A company representative came to our house in May 2005, and found that nine (9) windows had some degree of filming due he said to "inner moisture."
The company agreed to contact the manufacturer to obtain an on-site inspection, but a few weeks later, it was determined by the company that the manufacturer of Carefree brand windows had gone bankrupt and out of business. The company subsequently told us that it, therefore, would not replace at no cost any of the filmed windows, since the manufacturer was no longer in business. "I am at a dead end," we were told by the company manager, Mr. Mitchell.
We went back to the BBB with this information; the BBB agreed to try to arrange for arbitration of our case, but were met with silence on the matter. The case remains in an unresolved category.
To summarize my wife's and my position, we believe that, at a minimum, Consumer Construction, Inc. should be willing to replace at no cost the two windows that are completely filmed over, especially since the company's own inspector remarked, "You don't need blinds for these [filmed windows]."
Consumer Construction's position is unacceptable to us, as customers, and we believe it fails to meet standards of responsible business practice as well. Consumer Construction SOLD us windows that failed; THEY bear primary responsibility for resolving this case to our satisfaction. The company's position is like a food market telling a customer to go to the farmer who raised the steer from which a spoiled cut of meat was originally obtained!
(It would be interesting to know how many of the company's other customers have incurred problems such as ours.)
Ken Spalding Dale City, VA
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