Thanks for the comment! I went to my local hardware store (shoutout Mendards) to look into this more. After talking with the person there - I honestly think it's something that I can do - fairly easily. The jamb and the door hardware will just be switching places. Luckily, Menards sells a door Jamb kit (unfinished) in case I break it when configuring it all. All together, I think it will be a $75 project (high estimate) to do this vs $250 (quote for a new outswing door). Will update when finished (waiting til spring).
Re: the gaskets:
The gaskets are actually the same (per the person @ mendards and just comparing to what I have now), it just more depends on where they're located (inside the jamb for inswing vs outside the door for outswing). After inspecting the ones I have now, they are in dire need of replacing anyways (have entirely lost their 'spring' / compression qualities).