I finally had some time to troubleshoot the programming issue that I was having, and realized that the reason I wasn't able to connect to the chip is because the PCB i was using to hold the pogo pins had a defect and the ground plane was missing somehow....

Jump wire in place and now it works!

I am also planning on upgrading the chip to a STM32L031F6P6, for an increase in SRAM from 2K to 8K. The device should still be able to function with the originally intended chip, but bigger SRAM would allow to have the full display in a buffer in the MCU and allow more complex operations. The chip is pin-to-pin compatible, so there will not be a difference in the PCB design. The increased Flash will also allow the storage of few graphics on the MCU rather than the SD card.