Thanks for the responses everyone.

Deant, is it usually better to transfer Chase rewards soon, or to leave them in your Chase account until you decide which program you want to use them in. Regarding paying for the Medford ticket, I'm just trying to figure out my options right now. I'll pay for whatever I have to, but I'd like to stretch the miles as awesomely as possible.

akp, Costa Rica was actually one of the places that I was thinking about. I read somewhere that it's the rainy season in May so will want to do more research. I suppose this is kinda getting last minute, but since I only proposed in January, I think I'm doing pretty well Great tip on the free one-way. I'll look into that.

poser, Yeah, Medford is a pain to get to. Unfortunately when I've looked at other airports in the past, the savings was not worth the cost of renting a car and driving vs flying direct. C'est la vie...

tassojunior, I wasn't planning on churning, but I can see how this could be addicting

Thanks y'all!