Welcome, Scrimper, from a fellow transplant to Europe. I understand these things that are occupying your mind and don't have pat answers; but do have some questions.
1. If you are an American, are you ensuring that you are submitting tax returns to the US each year? Also, FBAR and FATCA reporting? Very important to pay attention to these things.
2. How much of the rental income is left over after your costs each month, if any? I ask because you need to think about the need to travel back to your native country for family emergencies.
3. You own two properties. How do you allocate funds for maintenance, emergencies, etc.?
4. What are the rules for citizenship in your new country? Is it a requirement for the free/reduced tuition in the universities there?
5. Assuming you are not living in a country where English is a national language (in southern Europe it would be Malta), where are you and your family in terms of acquiring the local language? Fluency would open up more doors for local employment, even if it differs from your current skill set.
Keep in mind that you chose a quite different lifestyle, where you traded some negative things (stress, not enough time with your family) for some highly desirable opposites (relaxed life, lots of time with your family). But with the new lifestyle benefits come a new set of negatives...such as the financial buffer you are missing. My suggestion is to treat this as a business problem -- how to create that buffer -- and soley a short term issue. Solve it by taking on part-time work, which you can do at home, if possible. Or locally, somehow. Once you are satisfied, jettison the work.
Wishing you the best on your adventure. BTW, what you are giving your children is amazing and very valuable. In fact, there is so much VALUE in your new life, much of which isn't generally amenable to valuation in the currency of the high stress/competitive (and sometime soul devouring) life you have left behind. Kudos to you and your wife for unlocking this value!
-BB