It sounds like your monitor has bad capacitors in the power supply that are slow to charge up. Repeatedly turning the power on as you do eventually charges them to the point where the monitor comes on. It isn't clear from your description if the monitor works properly when it finally comes on, so I don't know if it has other problems as well.
The shop you took it to probably didn't want to be bothered trying to diagnose the bad parts, because it's not economical to repair. They would need to charge you more for the repair parts and labor than the monitor is worth, and it's impossible to tell what other parts are ready to fail because of their age. I don't blame them. New LCD monitors are inexpensive, and it would probably cost less to buy a new one than to fix your CRT monitor.
My suggestion is to replace the monitor.
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