It looks to me that if I am flexible on destinations and dates that I should be able to stay in resorts using Last Call and Extra Vacations for $300 - $500 per week. My family could travel the country for less than I am currently paying for housing. When we are done we could settle down wherever we want.
Hey, sorry to be so late to the conversation. My family and I do exactly what you're asking about.
We have 3 sons (ages 8, 5, and 3) and we put everything into storage in July of 2014. We've been travelling ever since (8 months now). It's totally doable.
Here's the short version of how we do it ... let me know what questions you have.
80 - 90% of our stays come through RCI Extra Vacation sales for $209/wk. Most of the rest comes from Trading Places or DAE. We haven't yet found anything that meets our criteria from Platinum Interchange, but I check there from time to time. We are currently shopping for a low maintenance fee resort that's affiliated with II so we can join there as well.
We typically only book a condo if we can stay there for at least 3 weeks. Our target is to stay somewhere for 4 - 6 weeks. That gives us enough time to really enjoy a place and explore it with our kids from an educational perspective. Less than 3 weeks and we feel like we're moving out right after we check in, plus the first and last days of any stay when you have kids are lost to packing/unpacking/groceries/etc.
When we're planning our stays, we usually keep each stay within 500 miles from the previous one. That way, we can travel the distance in a day without too much trouble. Occasionally, though, we'll want to change regions and that's not as much of an option. For example, right now, we're in the midwest and in April, we'll be heading to Steamboat Springs, CO for a month. It's 800 - 900 miles, so we'll sleep in a hotel one night and check in a day late to our condo in Colorado. Keeping locations close to each other simplifies our life, so we don't cruise across the country more often than once every 3 months.
Everything we need fits comfortably in the trunk of our car. You've got more kids, so you might need a little more room than we do, but I've got to tell you ... there's something incredibly freeing about simplifying your life to what can go in your trunk (especially when you've got your homeschool curriculum and scooters for the boys packed in there too).
What questions do you have ...?