I've heard that shingles are very itchy and painful, so if given the choice, I would choose to not get shingles at all. Oh, wait, for the roof! ;-) I think if it's just $800 for an upgrade that should extend the life of the roof by 10 years, I would go with the upgrade and then just keep the spending belt extra tight for at least the next few months. Plus that extra income in July should help.