Long time lurker here. Thanks for the help. I just became premier Silver.

For the first half of the year, I flew a lot from Houston to Boston on Southwest for weekends. Sometimes, I would book in January for flights say in March for every weekend to have lower prices by booking earlier. I end up flying usually 2 out of 4 weekends, so I cancel half of my southwest tickets and get refunds from southwest.

I want to switch to United now. From September to December, I need to go to Boston at least twice a months on weekends. United IAH to BOS price when booked early is $250 or so, cheaper than Southwest HOU to BOS. And I want to go up to Gold or higher status on United.

But seems like I can not use my Southwest strategy anymore, because I will not get full refund from United. If I end up needing to change any of my pre-booked $250 flights, seems like I would need to pay for expensive change fee.

I have decided to fly United until I reach at least Gold for the year. For someone in my situation, someone who needs to fly half of all weekends to another city for visiting family member, but don't know exactly on which dates (because don't know which weekend will be free) what is my best booking strategy? Should I book all weekends for the next 2 months to get lower fare and pay for change fees? Or should I wait and book when I know with greater certainty which weekends I will fly and pay higher fare and less change fees?

I am so confused. I am spending a lot of my personal disposable income on tickets this year. Really trying to figure out best saving strategy.

Thank you so much for all your help!
Sorry for the long post.