Would you rather check or carry on in this situation?

Title: Would You Prefer Checking a Bag or Carrying It On for a Tight Connection?

A traveler shares a scenario: flying from a small-town airport (with a 50-seat regional plane) to Fort Myers, with a layover in Charlotte. The layover is about 50 minutes, and the traveler expects terminal changes based on the aircraft sizes.

Question: Which approach would you choose?
A) Check a bag and only bring a personal-item under-seat bag. This option offers the comfort and speed of getting to the next gate quickly, but carries the risk that the checked bag may miss the connection.
B) Carry a suitcase that must be gate-checked on the first leg. This ensures you have your belongings with you, but it can slow you down in Charlotte as you wait for the gate-checked bag and potentially makes the sprint through the airport more frustrating.

Costs for checked baggage are not a concern. The traveler is willing to pay for a bag to reduce the amount of items to manage during the layover, but fears the possibility of the bag not arriving on time. The question invites opinions on the best strategy in this specific scenario.

If you’ve faced similar connections, share how you weighed the trade-offs between speed, control, and the risk of delayed baggage. Include any tips on optimizing a 50-minute layover, terminal transfers, and handling gate-checked luggage to minimize stress and maximize the chance of catching the next flight.