American Moving to Ireland—Job Market Question

I work as a UX (user experience) designer in the US, and I’m sick of my current job and where I’m living, so I decided to change both of those things and move to Ireland, something I’ve been considering for years. I have done research on the immigration process, work visas, lower wages, higher cost of living, higher taxes, etc., so this isn’t just a snap decision—I’m aware it’s going to be difficult and expensive.

Although I think I would qualify for a critical skills work permit (web design is one of the highly skilled occupations), it seems like it would take a while to find an employer willing to hire a bureaucratic hassle who still lives in the US, and I’m still slightly under-qualified for the jobs I’ve looked at.

So instead of that route, I decided to get a postgraduate degree in the field in Ireland (I've applied at Trinity, NUI Galway, and Dublin Institute of Technology) to increase my qualifications. After that, the Third Level Graduate Programme would allow me up to two years to find a work permit. I am financially prepared to pay for school and to live on no income for a while.

With 6 years experience in the field in a high-paying UX job, an Irish master’s degree in a relevant field, another relevant master’s from the US, and a good portfolio, do you think I will be able to find work in the web design field so I can get a critical skills work permit and stay in the country?

And any other tips for an aspiring American expat?

Thanks!