My experience is in implementing java based enterprise applications, specifically in manufacturing sector, in product development (Product Lifecycle Management). This actually makes my skill set pretty niche. While I have had many opportunities in the US on the this skill set, it is very difficult for me to find options here in Canada. Hence, re-skilling myself is the best option in my opinion.
Also, on setting up the work with my US employer, my suggestion to anyone trying to go for this approach would be to ensure that proper transfer is done as soon as possible, to avoid any tax hassles.