First_ Principal I have been checking out pilots on conventional gear airplanes for over fifty years on everything from Cubs to the C117 and have learned that some of those who had the most difficult time getting comfortable with it ended up safer than some of the hot shots who did it in a short time.
The best benchmark for each of you is keep learning and then someday you may look back and be satisfied that you never let one fly you.
By the way my dream would be to someday own my own Stearman.....started my commercial career flying them crop dusting....