You are positive that it crashes? I have only seen that once or twice when repositories sent illegal responses instead of an archive listing.

Aborts are more normal, and indeed to be expected on a heavily packed tablet. All applications installed from file, anything originally broken (needing red pill mode), anything not available for OS2008 and anything vanished from the repositories between then and now must and will raise an error when you attempt to reinstall automatically. More severe errors (e.g. those with circular dependencies) will abort the install and require you to start over and unselect the package in question. If you have many of these problem apps about, it will make the process rather lengthy - but not really any worse than sorting it out with paper and pencil.