Soon-to-be Expat Seeks Advice on Pitfalls to Avoid

Hello!
My husband and I are in the process of preparing to move to Europe for a year. We currently work and live in NYC. My husband works with technology start-up companies and has considerably more job flexibility (and employability) than I do in my career as a school counselor. We are hoping to plan an August to August move that would see us living in various cities in the UK and Europe for a year.

I am now looking to you, experienced expats, for advice on how to make this dream a reality. My husband is looking to work to build his own company (he does consulting work for language technology start up companies) and I will hopefully find some source of income on our journey. This matter is further complicated by the fact that we only hold American passports and will not be securing visas. Our plan is to change cities every few months or so and to come back to the US approximately every three months to avoid immigration issues. We were hoping to start our journey by spending a few weeks in the UK while getting our feet wet and preparing to make our jump to the EU.

Any guidance or advice any of you could provide would be greatly appreciated! Our plans, as of yet, are loose to say the least and I know that it will lessen my anxiety considerably if I am able to gather as much information as possible and make connections with others who have taken a similar leap of faith.

I look forward to hearing from you!