I would like to suggest you that you should replace the window and get it installed by professional person. This will add beauty to your house, if possible. Or you can better take advice from any experienced home repair person who will suggest you the best. As you said that "caulking breaks easily and there are more joints than necessary".
Henry G. Clark
Posted 8:13 am, 09/15/2016
learn a lot, thanks everyone :)
Posted 11:42 pm, 09/11/2016
Thanks for your info Clinton. I just bookmark it for next time.
Posted 10:51 pm, 09/02/2016
I own my own home improvement company I will help if need just give me a call 3366200460
Posted 11:54 am, 10/29/2015
I have an old house whose unique house siding is no more available. It is 5.5" in dimension, thinner at the top, lapped down the end. It was designed in Atlanta.
Over the decade some of this things has been changed with thin cedar that does not range up well, so the caulking breaks easily, and there are more joints than necessary.
I was considering changing it in patching with 4x8 single part. I'd do this only where it would not make a long directly seem down the part of the house. For example, between windows less than 8 ft apart. So, it would just need to make a good end at the top and base, where it would fulfill the older window siding.
Are there any issues I should anticipate? I know it won't look great, but ideal looks in a house this old would break the line, and a water-tight external is more important.