Need help regarding company shares in-kind transfer

My company offers a shares plan (non-registered account) through SunLife and I have been contributing for the past year. And the details are as follows:

Total worth - $6000

Vested stocks - $4800

Unvested stocks - $1200

Total P/L - Negative $160

My company also offers TFSA through SunLife. The stock has been down about 10% over the past month. I have always been in the profit zone before the past month which made me think that I will have to pay a capital gain tax when I sell it. I feel the company will do well in the long run. I have a TFSA room of 13K, and I will be buying VEQT for $250 biweekly.

  1. I was wondering if I could use this opportunity to do an in-kind transfer from non-registered to TFSA so that I can avoid capital gains in the future?
  2. Is it a good idea to do an in-kind transfer now or wait it out until the P/L nears zero?
  3. Will there be a capital loss tax event if I do an in-kind transfer?
  4. The company will be paying a dividend this month so how does it affect the dividend if I transfer the stocks before it is paid?
  5. How does in-kind transfer work? Do they transfer the stock or will they sell it and buy the stock for the amount available?

Thanks in advance for taking the time to respond to my questions.