1) IT is a big sector. If you like assembling PCs, web development and design, those are quite distinct areas of IT. You should narrow down an area which you are really keen to pursue first.
Assembling PC: Anybody can do this and like it or not, you will face competition from foreigners for these jobs. In addition to IT graduates from the ITEs / Polys. Even if you stay one for 10 or 20 years, your salary will probably peak around 3k
Web Development: You mean coding? Then you need to ask yourself whether you really like programming. It is one of the jobs which doesn't need you to work with people, but it isn't for everyone and it isn't uncommon for many to drop out halfway through their studies
Web Design: These skills are easy to pick up on your own on Udemy, Coursera etc.
I really think you should narrow down which area you want to invest you time and money in first. Good that you are trying out the Udemy course, which employers will not look at, but it should help you in deciding your area of focus.
2) Will private diploma / Professional 'O' Level cert get you far?
Looking at the number of graduates with 'real' diplomas from the Polytechnics and ITEs, who are now also wondering if they can compete with the equally jobless fresh local university graduates, do you think the private diploma will help you land a job?
However, if the school running the private diploma /cert is reputable and you really believe it will help you build up useful skills, then it is worth considering.
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