They make a tool that you can use to remove caulk and as for the paint it's a matter of chipping it away carefully or using a heat gun....which you have to keep a good eye on so it doesn't catch fire. I see no reason that with a little patiences and time you can't remove the stuff that is keeping the windows close. I wouldn't change out the windows.
I'd work on as a seperate project from your painting.

Your outer windows can be gotten open but it will take some effort. However, it is well worth it, and is usually not a technically difficult project, though if you have a big sunroom, it may seem tedious. It mostly takes patience, and persistence, to break painted-in windows loose

You will probably have to loosen them from both the inside and out if they have been painted shut on both surfaces. There is a tool call the window zipper which may help, but I often find other tools from sharpened screwdrivers, to utility knives (hard to control safely, but sometimes just the ticket, especially with caulk), the 5 in 1 painting tool, assorted chisels, scrapers, etc. do work.

A heat gun (with a glass shield accessory) may also be invaluable to soften the paint join. You might also try various paint strippers (my current fave is Soygel), though these are harder to control on veritcal surfaces.

Resign yourself to going at it slowly, but steadily.

Your original windows are almost priceless since having appropriate ones made to match will be very, very, costly. If the windows are even passably OK, it's worth the effort to rehab them.

There is book, Working Windows by Terry Meany, that is still in print and the standard text for undertaking DIY window rehab.

The best thing about a window project is that it is one place where even someone with basic (or like me, primitive, when I started) DIY skills can easily learn to make good quality repairs. And because you do the same things over, and over, and over, on a window project one gets quite skilled. In some cities there are dedicated window-rehabbing contractors, but it usually costs a bomb to hire some one to do it, especially on-site. (Though getting a quote may spur you on when you're flagging and wondering why you started.)

Keep in mind you may have some lead paint issues: dust particals and paint fragments that need containment, and potential vapors if you use a heat gun or plate. Please, do not even contemplate using a torch, you risk burning your house down. As a PP noted you may risk that with careless heat gunning, but it's less than with a torch. Heat gunning (with a glass shield) should be OK if you just use it to soften the paint film enough to make it break more easily.

House painting is 80% prep work, and getting the windows in good, ready-to-paint shape is 50% of the prep.

If this is more work and time than you have budgeted for your project this summer, then try to do at least one window (on each exposure if there's more than one), so you can get some air circulation going. Then paint the others without breaking them open. Next summer you can go back and do the others. One extra layer of paint won't really be a big deal, nor would painting them again once they are open be a big deal.

Are your exterior windows hinged or hung? Keep an eye out for the screens - once you get things working you'll need them, too. In warm weather you'll able to use the sunporch as a sleeping porch, and fall asleep listening to the frogs croaking and watching the lightning bugs blink. Waking up on a sleeping porch just before dawn while still being snug in a comfortable bed is exquisite.
HTH,

Molly~

Hey thanks for all the great advice...I guess i know what I will be doing this weekend..housekeeping....by the way my windows are hinged.... Thanks


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Here is another shot of my windows.


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Those windows are way too cool to replace them with some newer cheapo version. It might take a while to get them done but that's part of old house ownership.

totally agree w/Carol
LOVELY windows - don't replace them, rehab them!

anyone have any ideas about how to repair the windows themselves? I have beautiful old windows, but some of hte glass is actually cracked/shattered. I'm considering just replacing them, but it would be nice to save the windows and just replace the glass.