Yes, very easy if in the past.
With the tighter regulation now, it's almost impossible if you are a new agent in both fields.
Juz to get the license for insurance,
MAS do a 'background' check on you nowadays, not counting the various papers u need to sit and pay for. Some of my ex-colleagues had to declare their other job positions and 1 of them took 4-5 months to clear, running up and down to settle the license just becos he is oso a sole trader in his other company.
Also heard of ppl failing to get their license becos they hav past records, from criminal to less minor like traffic fines (No relationship but still rejected).
The property agents are slowly being given the same treatment.
Btw, I was an ex-insurance agent who left last year.