First you, typically have to pick which brand/point system you want to go with - i.e. Amex Member Rewards (MR), Chase Ultimate Rewards (UR), Citi ThankYou Points. If you spend ALOT and travel a lot you may want to have two or more brands/point systems - but I personally went with Chase UR because the AF's are usually lower and there are more transfer partners. For example, Chase has transfer partners like Southwest, United, Hyatt, Marriott while Amex has transfer partners like Delta, Hilton, and SPG (although technically both companies have SPG and Marriott as transfer partners since you can transfer between these programs).
Once you decide this, then you need to decide what cards you need/want. With Chase to transfer to transfer partners (and this is where you maximize the value of your points) you have to have a card that has an annual fee, such as the Chase Sapphire Preferred (CSP), Chase Sapphire Reserve (CSR), Ink Plus, or Ink Preferred. You can pair other cards with these to maximize rewards, such as the Freedom, Freedom Unlimited, Ink Cash, but you have to have at least one of the first 4 cards listed above to transfer, else all your points can be redeemed for are cash, statement credits, or gift cards.
In order to maximize these points, you use transfer partners. For example, say your have 8,000 UR points. You could cash these out for $80 (since 1 UR is worth $0.01 when cashing out) or you could transfer these to Hyatt and stay at a Grand Hyatt that goes for $259, and since when you use points for a stay you don't get charged taxes or fees, the value is really more like $280 (you would have paid this if you paid cash). So, if you take the $280 and divide it by the 8,000 UR points you used to get that value, you find that you received $0.035 / UR, or 3.5x the amount you would have had if you cashed it out. That sounds great, right? Well, it gets even better. By maximizing bonus spend - such as 5 UR/$ on the Chase Freedom quarterly categories, or the 5 UR/$ for cell phone expenses on the Ink Cash, you effectively are getting 17.5% back on your purchases in those categories back as value as a Hyatt stay. Now, that doesn't mean every UR you transfer out will get $0.035/UR - some will get more and some less. I typically get $0.018/UR on Southwest redemptions, but if you fly international on United you could get over $0.05/UR doing business class.
Now, there are even more options and things to consider when doing point transfers - such as using points to purchase travel through the respective Chase and Amex portals to get better redemption values or to access travel that you might not be able to get using transfer partners. For example, I used my points to purchase airfare for Amercian - which isn't a travel partner - on the Chase portal because none of the other transfer partners offered flights for where I needed to go or if they did the point values didn't work in my favor. So I used my points at a lower value than I would normally get - $0.015/UR because the CSR allows you to get $0.015/UR when you purchase travel through the Chase portal - but I made up for it by scoring a room at a Grand Hyatt for 8,000 points that was going for over $350 a night (so $0.0475/UR there).
