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I never send cash in the mail. I've never tried it regarding autographs, but I've had negative experience with it for stuff like paying for photocopies from records clerks.
I know the post office discourages sending cash in the mail.
IMO, cash works best for overseas requests. That's what I use and I have an 80% success rate from overseas. IRCs are expensive and a lot of celebrities don't even know what to do with them.
I always note in my letters that I sent IRCs to cover postage to the US. The two times I've tried sending cash through the mail, to UK celebs known for being very good with fan mail, resulted in me getting nothing back. I've had way more success with IRCs.
In fact, I decided to crunch the numbers. Since I started writing again in May of 2010, of 17 celebs in the UK I sent to using IRCs, 13 have come back; 76% is pretty darn good, I think. That number will probably be higher, since several of those requests were just in the last two months or so.
2014 Successes: Tom Baker, Patrick Stewart (vv), Peter Cullen, Robin Atkin Downes, Jenna-Louise Coleman, Trace Beaulieu, George Lowe, Joe Dante, Willem Dafoe, Jeffrey Brown, Maurice LaMarche, Alan Oppenheimer, Penn & Teller (last success 10/14/14)
I've spoken to other members through PM, and it seems its half and half... and these guys have good results. Im thinking sending 2 dollars for the US requests is the easier option. I dunno...