I'm glad I bought mine when we were broke. I know she's occasionally jealous of these young girls getting silly rings, but I don't think it's a big deal. I've bought her other expensive jewelry that I've never seen her wear. Adam Ruins Everything had a show on diamonds that pretty much mirrors what Vid said. There isn't any actual value. Pinball isn't a fair comparison. I've made money on the majority of games I've sold. If I lost money, it's maybe 10%, 20% max. I'd be surprised if you were able to recoup 25% of the cost of a diamond.
I did however go all out on the proposal. I wrote a song for her and put it on a CD. When she opened the CD player the label said "Marry Me". The song also went on our next record. We were by no means successful, but she heard it at hundreds of shows. I think that is more memorable than just spending money.