About a week before I hit six months with Discover (my first credit card, opened in July 2013), I attempted a hard pull CLI. It was rejected, so I was still at my opening limit of $500. Just under three weeks later, I was granted an auto-CLI of $250, bringing me up to $750. I think that I probably would have received the automatic increase even if I hadn't asked for one with a hard pull, but I'm okay with asking for a hard pull on TransUnion.
My strategy for the Discover card is to ask for another CLI after my twelfth statement. That way my inquries are every six months, so only two will affect my score at any given time.
I think I'm going to follow that same strategy for my other card, the Citi Dividend. I opened that in November, so in May I will first attempt a CLI via soft pull, and if that doesn't work, I think I'll go ahead and take the inquiry. I only have two inquiries on TU (both from Discover) and one on EQ (from Citi), so I'm really not concerned about adding these single inquiries from time to time. I'm not looking to apply for anything major like a loan.
Anyway, I can't speak any advice about the Chase card other than that I've heard some people recommend having a year's worth of history before applying. The Freedom would be an excellent card for me, but I don't want to get stuck with another low limit -- but that's just me. I do, however, think it would be a good idea for you to find a Visa or MasterCard so you'll have something accepted in almost every store. This is why I went for the Dividend, because having a universally accepted card is most useful for online purchases, because if a site doesn't accept Discover, I can't exactly pay with cash.
I'd really like to hear about what you end up doing! Good luck with whatever you choose to do.
Discover IT $17k / US Bank Ace (VSig) $13.5K / US Bank Cash+ (VSig) $13.5k
