Outlook to Gmail headaches

Hello all,

[NOTE: I selected Google Apps because it was the only Gmail option available... this question is about a personal Gmail account.]

I am trying to help a neighbor with migrating Outlook email into Gmail. I was surprised by the roadblocks I hit.

1. I thought I could simply create a new (and temporary) Outlook folder linking to Gmail. Then copy the folders into the new Gmail folder to synchronize with her online account. She wishes to use only the web interface. Unfortunately, Gmail kept insisting that either the user name or password was incorrect... Tried all manner of settings (yes, Gmail settings were correctly enabled for both POP3 and IMAP)...
After giving up... and towards the end of my visit, an email from Google arrived that described the attempt to connect via an outside program. I didn't have time to read it but it basically described a security feature that needed to be enabled first, before allowing Outlook to connect! Grrr... I appreciate the extra security but do you think Google could have notified the account owner a little sooner? ???

Anyhow, can anyone explain what I did wrong or what I need to do to have a little success the next time I visit my neighbor?

2. As an alternative (because doing the same thing repeatedly and expecting different results....), I found this .pst import tool (https://tools.google.com/dlpage/outlookmigration). I had thought I found a PERFECT solution but after setting everything up, I was crushed when the tool needed an API enabled through the "admin panel". What? Doesn't this .pst to Gmail import tool work with personal Gmail accounts?

Is there a .pst to Gmail import tool that works with personal Gmail accounts?

Can anyone help with either option? I prefer option 2 but any solution will make me happy. :)

Thank you,
Shawn