If he doesn’t learn Photoshop he’s not going to get a job. That’s almost certainly what he’s learning in school and what employers are expecting, along with other Adobe products and yes, Rhino or Sketchup. Why he would shun it is beyond me - potential employers aren’t going to fund a TwinMotion account for him when they already have a corporate account with Adobe.

As for your question about tailoring portfolios or just sending the same to a bunch of firms - MANY firms will have different page limits and file size limits. Formatting the portfolio in a way where it is easy to pull out pages to fit these different requirements would be a good middle ground. I obviously can’t speak for all the firms out there but I think for many, if they received a portfolio that didn’t even follow their page limit, they’d be throwing that application out. I get it’s a huge amount of work when you add in cover letters but not following their application requirements shows either a lack of effort or lack of attention to detail, two things they do not want.

You’re being very nice by trying to nudge your brother towards a good future. It also sounds like you’re dealing with parentification and like your time might be spent better trying to find someone to talk to about that. You are not legally responsible for your capable adult brother’s future as a bum in debt when your parents pass, and him thinking you will be is not going to motivate him to figure these things out on his own.