US->CAN: Roth 401(k), Roth IRA, Rollover Timing and RSUs

[flyingmonkey]

Hello. I am a Canadian citizen, moved and am working in US under a TN visa since Aug. 2016. When moving here I was given the financial advice to hold onto my money and not invest until I was settled and had a good idea what my plans were. At this point I am ready (and have money) to start investing so I have done my research and looking for a final bit of advice and/or confirmation.

My current plan is to move back to Canada in roughly 1-2 years. Based on this and what I have read here and in other places regarding taxes, it would be best to focus my money into Roth accounts, both Roth IRA and Roth 401(k). My employer offers a Roth 401(k) but does not offer matching. My gross income is also relatively high, and my contribution limits to a Roth IRA may be heavily reduced if not nil.

My plan is thus the following: Deposit $5500 into a Traditional IRA and immediately rollover into a Roth IRA (Backdoor Roth) since I currently have no other Traditional IRA accounts. Open a Roth 401(k) with employer and max it out. Any leftover money I will invested in a normal taxable account. My current plan is to just open a Vanguard account for the IRA and taxable account (i.e. nothing US/CAN specific).

When I decide to leave to go back to Canada I will do the following: Transfer Roth IRA to a brokerage that is happy dealing with Canadian residents. Quit job. Rollover 401(k) to Roth IRA (put everything in one place). Empty taxable accounts and move them to Canadian investments. This way when I am back in Canada my only US accounts will be Roth retirement accounts with a brokerage who can handle Canadian residents, so it should have minimal tax reporting implications and I can handle like other retirement accounts. As I understand I only need to report to CRA the Roth IRA on a single form, once, then I leave it untouched "forever".

Questions I have:
1) Does this strategy make sense based on the perspective of avoiding serious tax implications or problems when I move back to Canada?
2) The timing is one thing that worries me. From my understanding I have to do all of the rollovers before I move back to Canada. I cannot rollover my 401(k) however until I quit my job. As soon as I quit my job however my TN visa is no longer valid. Therefore, is it possible for me to rollover my 401(k) after I quit considering my TN is no longer valid? My assumption is that from a Visa perspective I am not a US resident at that time but will still be a US resident for tax purposes until I physically move.
3) One other question is that I am receiving private RSUs from the company I work at. There is no way I will be able to sell all of my RSUs before I leave as the sell opportunities are few and far between (once every two years or so). Are there any implications of holding onto RSUs from a private US company while in Canada?

Thanks!

[nelsona]

Once you quit, you simpky apply for B2 status to wrap up US affairs. The key is getting all these things done before establishing CDn residency.

RSUs will be taxed in US first with Canada gv=iving a tax credit.

Everything you said makes sense. Although I probably wouldn't bother with the 401(K), just do the Roth 401(K).

[flyingmonkey]

Interesting, the B2 status, never thought of that.

When I said 401(k) I meant my Roth 401(k). My plan is to only hold Roth accounts (and a traditional IRA for the short time I need to do the backdoor Roth IRA).

If you don't see any flaws this is what I will do.

Thanks for the help!

[nelsona]

if you are doing a Roth401(K), then there is no timing issue with respect to rollover to a private plan, since moving the account from one Roth to another can be done anytime before or after moving to Canada, with no consequences.