Currently I have a roll model that is facing a few months in jail and I wondered if it would be a appropriate or not to send a letter or if they would find it odd. What do you think I should do?

Your "roll model" is hurting now and probably a little embarrassed to hear from you. BUT, we are in favor of reaching out in times like these. If your instinct is to contact them, then follow that. Your sincerity and willingness to initiate communication is a great thing.