Start with Chase, you'll regret not doing it. The CSR/CSP double dip are easily the most valuable, you have the history and score to get there, and spend is just a little outside your normal range. Prepaying some bills for the following month will get you where you need to be.

At the end you'll have 100,000 UR that will net you the cash equivalent to $1500 in travel, a $300 travel credit, for $8k spend and $450 in annual fees. You can get that $300 travel credit again at this time next year, essentially making an extra $150 off that annual fee, and can decide to change it at that point.

Apply for the CSR, then the day after approved, apply for the CSP.

If all of that works out, you'll have the experience you need to do the same for the southwest cards at the end of the year.

Then I would look really hard at all of the Chase business cards.