There seem to be a lot of rules or specifics about this so I won’t even try to summarise:
Introduction This information is about the EU Settlement Scheme for applicants with a criminal record. The EU Settlement Scheme protects the rights you currently have in the UK through the process of applying for settled or pre-settled status. As part of the applications process, there are...
unlock.org.uk
I’ve heard of some people being refused settled status due to their criminal records but I don’t know the details
Student Finance probably - I don’t remember on the top of my head but EU nationals living here had to jump through a bunch of extra hoops to receive finance, pretty sure now it’s enough to provide proof of pre/settled status but I may be wrong
No extra details seem to be known about his homelessness - when it started or why