Welcome to the site. There is so much to address in your post and only two weeks to do so 
. Be aware that you can search threads here and find a ton of info for any recruiting question. Congrats to him on the offer!
Answers to most of your questions require more questions. Why does he aspire to go out of state? Is that a dream with depth, something that has been researched? Or is it more superficial - wants to get away from home, admires the power 5 schools he sees on TV for the CWS, etc.? If he is targeting HA private universities, this won't apply but there is much written here about in-state vs. out-of-state costs and recruiting challenges for the recruit as well as the school.
Regarding the opportunity to showcase - you say he is playing football. Is he still baseball sharp? If he has not been also staying baseball sharp during football season, it's may very well not a good idea to attend a showcase, particularly as a P. I say this from both a performance and arm safety standpoint.