I'm using Questrade, and because I have a self-directed account, I need to put in a buy order manually 1x/month. Is that the way it's normally done?

I used to have a mutual fund through my bank, where I'd set a monthly amount and they'd automatically deposit that into the fund from my chequing account. I decided to try something different since the reporting tools available through the online banking system were very basic.

Cheap Vanguard funds like VFIAX (S&P500) or VTSAX(Total US stock market). No need for managed funds that charge over 5 basis points, you're just wasting money. Then sock away cash in a no fee online high yield banking account like Ally or Marcus.