Here is my very brief version of the rules I keep in mind when planning a trip/pursuing sign up bonuses.
1) Choose a destination
Know where you want to go!
2) Decide whats important
Flights? hotels? both?
3) Research, research, research.
There are a ton of great points and miles websites out there. Familiarize yourself with them.
4) Figure out what points you need for the trip.
Specific hotel cards? Transferable points? It's likely a combination!
5) Don't buy anything you can't afford & pay your bills in full & on time.
I can't say this enough. Any bit of interest eats away at your redemption value!
This hobby is about taking trips you wouldn't otherwise be able to take! If you get yourself into debt in pursuit of this it defeats the purpose of this hobby. Don't. Buy. Things. You. Can't. Afford.
6) Stick to a plan.
Earn bonuses as you are able to. It can be tempting to spend those points as they hit your account, but stay focused! It can also be tempting to get a different card as soon as a big sign up bonus is released, but make sure this card fits into your overall goal.
7) Don't miss that bonus or lose your points.
Know when your sign up bonus earning window opens/closes. The clock often starts ticking the day you're approved! Your card issuer is always happy to let you know the exact date.
Also- when canceling a card, be aware if you'll lose the points.
8) Fees, fees, fees
Many points/miles cards come with an annual fee. Make sure you're making the most of every card in your wallet. If you're not getting more value from the card each year than the annual fee, it may be time to dump it.
Know if your card waives foreign transaction fees. It's not fun to see fees pop up on your vacation purchases!
9) Pick a card with trip protection.
Let's be honest- Delays and cancellations happen. Luckily cards like my Chase Sapphire Preferred and Ink Business card both cover those!
Last year while in Chicago for my husbands birthday (& Star Wars Celebration!) our return flight was cancelled due to snow. I had booked our flights using points, but luckily paid the $12 in taxes/fees with on of my Chase cards.
Instead of stressing we were able to re-book our hotel & enjoy a relaxing day in Chicago thanks to the $500 per person reimbursement limit!
10) Enjoy your trip!
You earned it! Have fun & start planning the next one when you return!