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Hi Sean. Fellow Canadian here. We're relocating to Tamarindo in July.

I'm presuming the context of you listing your skills is to ask if you'll be able to find a job? You should be aware that getting a work permit is hard, but not impossible. You have to prove that you have skills not readily available in the Costa Rican pool of employment candidates. This is where a good lawyer can help, but you'll still need a job offer.

Do you speak fluent technical Spanish? Do you have knowledge of Costa Rican construction code and laws? I'm no expert, but I would imagine these are prerequisites for a lot of the sectors you mention.

You can look at a self-employed visa too.

Not trying to rain on your parade. But bear in mind that a lot of expats are coming here on rentista and pencionado visas rather than work permits.

Suggest you also read the info on the to get additional information.
While , it will not provide eventual Permanent residency which will take 4-5 years from your initial application at this time.
When applying for residency in the Rentista category, please note that your mandatory, monthly  healthcare premiums, if under 55, could be in the $400+ range.
You cannot have a work visa and Temporary Residency at the same time.
I, too, am Canadian and I lived there for 18 years. However, it is not cheap, especially with 4 children to be put through the education system, as most of the expats that have young children choose the private schools.
New rules regarding residency are supposed to be 'in the works'.
Also strongly suggest you read the info on becoming a ' to see what benefits you may lose...

Costa Rica is a great place to live...if you can afford it.

Good luck!

@eekageek Thanks for your help. Your reply is not a torrential downpour, it just means i wont be going there as quick as I'd like to. Thats ok. I have taken spanish in high school, but dont speak it fluently. I do have hispanic coworkers with whom ive been able to converse very basically with.
A big move like this takes a lot of careful planning, especially with the kids. My 2 older kids are actually from another lady, and I'd need a lot of legal work done for them to emmigrate canada.
Thank you for your pointers. They are very helpful.

@kohlerias thank you. That is also a big help. The medical coverage doesnt bug me too much. Its not much more than ive had to pay when i used to be self employed.

I should have added that most expats also purchase private health insurance due to very long wait time for specialists, specific tests, etc...and of course the monthly premiums are in US$ funds which really hurts the Canadian budget.
Your dependents must still be under 18 by the time they are approved for Residency or attend university full time in Costa Rica, and they can't legally work  until they have gained Permanent Residency which I previously mentioned, can take at this time, 4-5 years from the initial application. If over 18, they are required to have their own CAJA account, which means that they must apply for Residency under the same financial requirement as yourself and incurs lots of additional US$'s 

@kohlerias. Yikes. It just adds up and up. But alas. So do canadian taxes and fees.

What i enjoy most about infrastructure work is theres always more and more need for skilled workers and not every country has those skills