Originally Posted by
hotturnip
A more realistic goal might be to buy one ticket with points and purchase the other one normally. There are often good sales on premium fares throughout the year. Then you would actually earn a bunch of miles on the purchased ticket.
I would just warn that this might actually be tricky to do -- in many cases, the routes that have saver-level awards available have very expensive cash rates, and ones with very cheap cash rates have no saver-level awards available.
As an obvious example of when this would occur is for last-minute bookings.
I'd personally just recommend getting several CC sign up bonuses, and making sure that you plan it out that you are only spending on the CC what you would be spending anyway -- most of your daily spend other than rent/mortgage/loans can be put on CC -- think utility bills, insurance, cell phones, groceries, gas, tolls, restaurants, etc.
I find that with a fairly normal amount of spend and some planning it really isn't that hard to rack up a half million points overall in a single year.
As far as airlines to fly in a premium cabin internationally, I'd highly recommend looking at international airlines like ANA, JAL, Singapore, Lufthansa, Etihad, Emirates, Cathay. There are other airlines too which are not quite as good as these, but are still substantially better than UAL, DL, AA. Also keep in mind the concept of "Fifth Freedom" routes, for example Singapore Airlines flies from JFK - FRA, and Emirates flies JFK-MXP.
Note that through UAL awards you can book flights on any star alliance partner.
I haven't personally used any Chase points yet, but have racked up ~400k points so far which I will be using for (something) at (some point).
My strategy has been to earn points through multiple programs simultaneously which allows for lots of flexibility in planning trips, and it seems that even with planning a crazy 5-star trip every year, I never run out. At this point, I have 6-7 figure points balances with Amex, Chase, AA, and Hilton. I wouldn't really recommend trying specifically to earn a large Hilton balance, that sorta happened "by accident" in my case.
Also, plan that you will likely have to pay cash for an economy-class positioning flight to get to the international premium cabin award, and make sure you have enough time between the two flights to give a good buffer in case of a delay, since you aren't protected from a misconnection if you have two tickets. On roughly half of the big international trips I've done, I was not able to find awards on the domestic leg, so had to pay a few hundred bux and tough it out in economy before connecting into first class on a 4-class 777-300ER.
After earning the bonus from the Reserve, I'd suggest looking towards signup bonuses from Amex Platinum, Chase Sapphire Preferred, Chase Ink, and the quarterly category bonuses from the Chase Freedom (points, not cash) card. Right now the bonus category is for groceries at 5x. The Chase Reserve is always 3X at restaurants. Amex Platinum is 5X on airfare. Citi's AA cards also have reasonable bonuses, and are useful for oneworld partners.
The Citi Prestige card also offers "4th night free" at any hotel in the world, so this is also potentially a great combination in planning a trip, or earning status.