Is it actually legal to download proprietary programs available from "abandonware" websites such as http://www.abandonia.com?
Furthermore, If decide to decompile a program obtained from such a website, with a tool such as Boomerang, would I be able to make my own modifications and distribute it under a free/Open Source license?
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4If the copyright has actually expired, the software is legally in the public domain. You can't (as far as I know) just slap your own license on a public-domain work, but if you make a modification, you can copyright (and then license) the resulting modified work as your own.
The hardest part, then, is determining the legal status of the software. This will actually differ from jurisdiction to jurisdiction; you only need to worry about the jurisdiction you are actually in.
Also, many of the older games don't have EULA's, or have very simple ones. It's probably not against the terms of the license to decompile the code. Once you've gotten that far, you can edit the program all you like as long as you don't distribute the modified code. At the very least, you can learn a lot about old games this way. Then, if your modifications are significant enough, you can legally claim to have made a new work and copyright it yourself. This is tricky, and you should definitely consult legal counsel before commercially distributing these - but if the game is abandoned in the first place, chances are very small that you will be called on any small discrepancies by the copyright holder.
1) No, it's not legal unless the copyright holder says you can. They're probably not available to ask or not interested in giving you permission, though.
2) Given the answer to 1), then no, it's not legal to make a "derivative work" and pass it on, again unless you have the permission of the copyright holder.
That's what copyright means - the right to control who can copy the work to which you have rights.
Whether in most cases of abandonware the copyright holder has any interest in stopping you doing either of these things is a different matter.
Legally, no you cannot. I don' think any copyrighted software has been around long enough for the copyright to expire. Advocates have been asking Congress for an "abandon software clause" for years, but congress seem to have little interest. As far as I know this is the same situation in most if not all countries.