It is actually a very simple firmware fix, you only need to change one line in TinyTV2.h:

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#define MAX_VIDEO_FILES 100to

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#define MAX_VIDEO_FILES 200
I compiled it and uploaded it to my Tiny TV 2. It works without any issues.

+1 I would also be interested in this.

@NatetheMac
@ang-tinytv

I'm using HandBrake to convert my videos from MKV to MP4 first, with a resolution of 216 × 134 pixels, a variable bitrate, constant quality set to RF 20, and the audio track set to AAC Mono at 128 kbps. After that, I convert the file with FFmpeg using the following terminal command on macOS:

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ffmpeg -i input.mp4 \
  -c:v mjpeg -pix_fmt yuv420p -r 24 -s 210x135 \
  -c:a pcm_u8 -ar 10000 -ac 1 \
  output.avi
What works even better for me is adding the quality parameter (-q:v) and setting it to 1, which noticeably increases overall sharpness. For most videos, setting it to 2 should be fine as well. Also there is a volume parameter (-af "volume=[val]dB")  which might come in handy:

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ffmpeg -i input.mp4 \
-c:v mjpeg -q:v 1 -pix_fmt yuv420p -r 24 -s 210x135 \
-c:a pcm_u8 -ar 20000 -ac 1 -af "volume=2dB" \
output.avi
Interestingly, setting the audio sample rate to 20 kHz works just as well as 10 kHz, and my TinyTV 2 still plays it without any issues. I thought higher sample rates weren't supported, but it seems like they are!