Where To Go
Some background about me:
I'm a US citizen.
I have been self employed for over a decade (consulting). I have an LLC, and my business is entirely online.
My wife and I are in our early 40's and we have a 5 year old.
My wife and I have traveled extensively throughout Europe. She speaks English and Tagalog. I can speak some Spanish.
Edit: Thanks to everyone who has responded. I added some additional info below.
I operate a marketing agency. I have 20 years experience in marketing and related tech, and I started my own company over 10 years ago.
I have completed some college, but I do not have a degree. My wife has a Masters.
No criminal record. I'm too far removed for Italian or Irish descent citizenship. My wife is from the Phillipines, but she's been a US citizen since 2005.
I'm more interested in what makes the most sense logistically. Culturally I could make it work in many European countries. I'm partial to Portugal, Spain, Netherlands, Ireland, Italy.