1. Use Google flights (though SW isn’t visible so it’s best to check them as well if they fly the route) as a base to look at paid flight options starting from multiple airport options near you and going to multiple airport options surrounding your destination if both are applicable. Also use it to see the best dates for going places, where you can save more than hotel costs by going a day earlier or later at times. I recommend using $ whenever you are unable to use points to get above the TPG valuation on the best points option possible for a given itinerary.
2. Use some of the best options available for acquiring frequent flyer miles, especially through credit cards as long as you are getting the right cards (Free consulation with me), not ever carrying a balance, and have solid systems in place (my advice) to not spend more than you would if using a debit card.
3. If your dates are flexible and where you go is flexible, sign up for $ bookings for (paid or free version of) https://scottscheapflights.com/
4. Look out for fare sales whether w $ or w points (see points promos for flights)
5. There are some excellent groups on FB for maximizing as well as websites with solid updates for some of the best deals, like the 5 websites (Ask Sebby, The Points Guy, Doctor of Credit, One Mile at a Time, & Million Miler Secrets) I mention with links besides “Articles to Check” & more under “Social Media” here which include my FB group.
6. Some points have solid buying options in certain cases, such as when points are being sold during a promo of some kind where they are lower than The Points Guy’s valuations for that points currency (if available, & if not, check valuations of others I mention on my main page like One Mile at a Time. The highest tier of Club Lifemiles (which can be used on saver fare United flights & some international carrier flights) is one solid example for ongoing points purchased below TPG valuation.
7. When solid transfer bonus opportunities come around from Amex Membership Rewards, Capital One Miles, or Citi Thank You Rewards, there are some great opportunities. Check historic bonuses, making sure that you will regularly have good use of the transfer bonus compared to alternatives, then make the transfer ( history of points transfers). Be sure to keep the points alive since many expire unless there is some sort of activity and with some points there is no way to keep them alive after a certain period of time.