CPT to H1B timing

I have a computer science degree from a US university and I used up the OPT option couple years ago for a J1 job. Now I wanted to switch to a H1B job but due to the April to Oct gap, it’s hard to find an employer who is willing to wait me for 6 months, not mentioning that I might not get picked in the lottery.

My plan is enroll in a second master program which would allow me to do CPT from day 1, so I would have a chance to work in companies. My goal is impress the employer during CPT and have them apply H1b for me directly, I have no desire to graduate the 2nd master.

If starting CPT in January, I could ask them to apply H1b for me on April in the same year. Is it gonna be too soon? Should I start from a summer and work my way to next April?