I've found travel hacking to be much less hassle than I expected. I would start with a single card, get the hang of it, and then decide if you want to add another. I use the transfer system between Freedom and CSR because I just happen to have both cards and the Chase website makes it ridiculously easy to transfer in like two seconds.
Basically, I did this order of operations:
- Open a Chase Sapphire Preferred, get the 50,000 bonus (this was like 18 months ago). The annual fee is $95, waived for the first year.
- When the Chase Sapphire Reserve card came out, I opened that, got a 100,000 bonus.
- One year after I opened the Preferred card, I downgraded it to a Chase Freedom to avoid the fee.
Since I have run the numbers and determined that the Reserve card is worth the fee for my circumstances, I have a Freedom and Reserve open for the indefinite future. I spend like this:
- Is it a travel or dining expense? If so, put it on the CSR for 3% points.
- Is it on one of the rotating categories for the Freedom? If so, put it on the Freedom for 5% back.
- Is it something else? If so, put it on either one.
Once a month, when my Freedom statement hits, I transfer my Freedom UR points earned that month to my CSR UR account, because then if I spend them on travel I get the 50% increase. You could easily ignore this for months on end, and only consolidate points when you are about to buy a plane ticket.
As a super no-pressure aside - if you happen to decide to get a Freedom card, and are interested in using my referral link, PM me. I'd get $100 cash back on my statement. It markets it as you getting a $150 bonus after spending $500, but I'm pretty sure that's just the standard account opening bonus for the Freedom card, so really it profits you nothing, sorry :)
EDITED TO ADD: Because Chase has such great sign-up bonuses, they are pretty strict on only approving you if you have opened (or been an authorized user on) less than 5 cards in the last 24 months. Because of this, I am pretty careful not to open any cards that won't be super worth it. So, I would NOT recommend getting a Freedom card right now if you want to travel hack, because it doesn't have a good sign up bonus. I would sign up for a card with a good sign up bonus with the annual fee waived for the first year (such as the preferred card), and then downgrade it to a Freedom card right before the first annual fee hits. In this way, you would be getting the benefits of a bonus-yielding card, but effectively making it so you have a no-fee card.