My understand of how it works is that you let them know the amount now and at the end of the quarter they take all of the money you set aside and buy the shares for you. So if you sign up for SIP today it won’t mean you necessarily receive your stocks at today’s price x 0.95… I would think of it as: will I be here for two more years? And also a bonus question: if I’m buying stock, am I willing to not spend any money at the company to maximize my investment? I bought SIP despite not planning to be here for much longer *just in case*

i would say wait until after the holiday season before any new seasonal drops so the price of shares go down, then buy, you’ll be getting a better bang for your buck if you wait until the next holiday season.