This was enlightening thank you, but also kind of shocking.You can leave and come back to Canada without any problem if you have a valid TRV and WP.
The only thing you need to consider is to come back before the expiry of your current WP.
If it's passed, you'll be allowed to enter with the proof that you've applied for the extension but you won't be able to work anymore until the decision is being made. Therefore, you need to show enough funds to the border officer for the duration of waiting period.
The TR2PR application is useless for you now because you haven't received an approval yet. Therefore, you need to rely on your TRV and WP.
I would think that I would be in the "implied" status since I am working + have applied to both PR and WP extension.
1- Are you sure I won't be able to work at all after my WP ends?
2-How do I calculate the funds? even for a few months I believe I have to show something like $1000-1500 a month worth of funds?