Don't transfer your points until you need them. Leave them alone to provide you the most flexibility.
Try to get $1.5 cents per point when redeeming to know that you are getting a good deal.
The more flexible you are with your dates and/or locations, the better value you will find.
Try to book the main flight first with flight. This is generally the most expensive. Then for shorter legs, the cash price may be cheaper.
Once destination is determined, figure out what airlines go to that airport so that you can see where you will need to transfer points.
As of now, Hyatt seems to provide the best point value for hotels.
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If you look here, you can see different examples. The point amounts can vary widely due to many different factors. There is no specific number of points that you need to have.
Credit cards are a great place to start (Chase, American Express, BILT, and Capital One), however you could have points at hotels or airlines that could also be leveraged. These all can have different redemption values so it's important to check the cash price to the amount of points that are needed to determine if it's a good deal.
The quickest way to get many points is to leverage a sign-up bonus from a credit card. Here you can find some different recommendations on how to do that.
*Please note, you should be in good financial standing before opening credit cards. These sign up bonuses require a certain amount of spend before you unlock them.