The problem with his description of his achievements is that he is probably underplaying them. Obviously without knowing what he has actually produced (seen the site, reviewed the code etc) I was hoping to make him see what he has done in a better light. "Spent two years converting a static website to something more modern" sounds really lame and could indicate a lack of confidence in what he is capable of or perhaps he is failing to recognise what he has actually done.

His CV needs to get him an interview and I think he is selling himself short.

Personally 'junior' means 'trainee'. Anyone who after five years is still a trainee would have their CV thrown straight into the bin. But I have always worked in environments with very flat hierarchies. Juniors need supervision and mentoring, I expect anyone who been employed for more than a year to be capable of unsupervised work.

Disclaimer: I am the IT manager, I review all the CVs, I get to say who gets employed. I've yet to regret any hiring decision so I am reasonably confident in the methods I employ.

I've employed people with much less experience than the poster and they were up to speed in no time. In 5 years you could get a degree in almost any subject and complete a masters on top of it - at least in the UK.

I would expect competence in a programming language in weeks or months, not years. Note I require competence not expertise.