I was approached (by email) by a whole stack of con-artists telling me they could guarantee me success in getting bigreddesign.com when it expired. They contacted me because I already had bigreddesign.co.uk.
My solution was to maintain radio silence, set a reminder in iCal for the end of the grace period, then register it myself the moment it became available via my normal hosting provider. It worked and I didn't end up paying hundreds of pounds to do it.
Given that you have at least as much chance of capturing the domain as anyone else (probably more if you care about it) I'd recommend that for anything that's about to expire.
As far as "novelty" TLDs go, I'd avoid them unless you come up with a really good
domain hack and even then I'd have a .com as well. Use anything other than .com or .co.uk and people start to get confused.