Upvote:2
For the purposes of bringing this question to an answered state...
The OP joined a bespoke chat room and engaged with Flimzy (to whom thanks) for about an hour. The OP left the chat satisfied and Flimzy was invited to provide an answer here.
The OP's friend will face a perilous landing interview: he is unemployed and without a permanent residence stateside. These introduce the risk that he will abscond and go underground looking for work. This risk is complicated because he has access to someone who is simultaneously at risk of harbouring him unlawfully and helping him eventually build up a case for settlement. On the plus side, the OP's friend appears to be well-minted and this will be taken into account.
Although the OP's friend does not need an entry clearance, he should bring all of the evidence needed to secure an entry clearance.
Performance in the landing interview is largely governed by personal impact and articulation skills. If the OP's friend is not successful, he will be removed under Paragraph 320 of the rules.