I remember trying all those things, and spent time on Google finding solutions. Eventually gave up, and changed to OS to XP professional as I have a couple of original ones which I bought on special.
Dropbox - Ending Support for Windows XP on August 29th
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Victor - Knowledge is a blessing or a curse, your current circumstances make you decide!
Solar pumping, Solar Geyser & Solar Security lighting solutions - www.microsolve.co.za -
If what you're concerned with is that a CMD window in XP having wider lines and more lines than the DOS standard 80x25, then that's because in XP you're no longer in a "true" DOS environment.
That limitation you find in DOSBox is a DOS limitation. There were additave programs which you could install into DOS to increase its limits. But usually you didn't bother, as the programs you ran did their own thing anyway. And since DOSBox is quite literally attempting to make a "true" DOS, instead of a DOS window into Windows' command-line, those limits then also carry through.
So yes, XP is probably your better alternative here ... that is if its DOS emulation (note XP is based on NT - thus it's not running on top of DOS like W98 used to do) actually works for your program(s). Personally I've found issues with even XP's variant of DOS, and had to revert to W98 instead (i.e. Windows is simply a GUI running on top of a fully fledged DOS instead of a DOS emulation running inside of a WinNT kernel).
I would however suggest you run your XP through a virtual machine, just to be more "safe". Instead of having it run directly on the hardware. XP is discontinued, thus any and all bugs it had will never get fixed. So if some black-hat cracker decides to write yet another virus / spyware / ransomware / etc. for some fault in WinXP, you've got no chance of such ever being stopped. At least with a VM it means your entire PC isn't screwed over all at once. Worst case would be that just the VM is damaged. And if you set it up right, you may even protect your XP from getting infected instead of trying to fix afterwards.
I.e. make use of a more current OS (need not even be a Windows) for your internet connection so you can sync with dropbox. Probably add some intermediary AV (like ClamAV) to check those files so they don't contaminate anything further. Then have your XP virtual machine able to link to that shared folder through SMB/CIFS shares - i.e. it can see them as a network connected drive. This would quite literally be like running XP on a separate computer which is firewalled from the internet, only able to see some shared folder from a local server - which itself can connect to the internet. Only with such VM you only require one computer, not two. Of course it's slightly less convenient if all you want is XP and whatever programs you run on it, but it's safer than even an AV running on top of XP.Gold is the money of kings; silver is the money of gentlemen; barter is the money of peasants; but debt is the money of slaves. - Norm Franz
And central banks are the slave clearing houses
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