@mhartman09 You're welcome! It does take a little bit of effort and does seem overwhelming at first. However, there are big pay-offs with even a small bit of effort. Compared to the bloggers who write about this stuff, I barely have a clue what I'm doing. Yet, I consider what we have managed to accomplish a huge success! I can only imagine what things might be like if I actually put some real effort into this hobby. I am thankful to the bloggers that do this for a living and share their strategies.
All things being equal, I would prefer a non-stop flight. There are circumstances that I would purposely book a connecting flight in lieu of a non-stop. If MIA had a non-stop to HNL on a plane that does not have a lie flat seat in the business/first cabin I would not book that flight. That is a loooong time in a reclining seat. No thanks. I would intentionally find a connecting flight in DFW where I know they have a plane with lie flat seats and book that flight instead. So, my first concern is always how long is the flight and what are my seat options. This is mostly because DH has turned into a seat snob

and I'll admit it's rubbing off on me too

If I am going to connect then I will look for the flight that offers me a reasonable amount of time to connect should there be a delay and that has plenty of other connecting flight to my destination. I prefer no less than a 2 hour window when possible. If we are on time, then I will go to the lounge. We bring all lounge access cards with us. That will include, DH's Chase United Club credit card which we keep just for the lounge membership, an American Airlines Executive card which we also keep for lounge access, an Amex Platinum card which will cover Delta and Centurion lounges and the Priority Pass card from the CSR since it has the best lounge access. This way, no matter what terminal we eventually wind up in at a given airport, if they have a lounge we are getting in.
Clearly, we like lounge access and if DH is willing to pay for those AFs to get it, well I'm not gonna complain

Seriously though, as our travelling habits increased due to this hobby we began to appreciate the benefits of some of the super high AF cards beyond the bonus points. Keep in mind we started off with the goal of one big trip and getting the best bang for our buck too. That was 5 years ago. Now, we take 2 or 3 big trips and numerous long weekends throughout the year.
@Lain mentioned dining at French Laundry in an earlier post which is on the bucket list, so now I am toying with adding another day when we go see Hamilton in San Francisco this July or simply booking a whole other weekend to San Fran just to do that! So thank you for that
@Lain and DH thanks you too, only he doesn't know it yet LOL 5 years ago I would have said that was crazy and so was making a transcontinental flight to see Hamilton, much less a transatlantic flight to London to see the Harry Potter play. Now, it doesn't seem as crazy to me. So, beware that this hobby can take you in directions you never expected. Getting the best bang for our buck still falls into our Venn diagram but a larger portion of it is what experience do I want to have.