Longer term financial planning

We're at that time of year where I get all anxious about our financial planning beyond just the month to month, or even looking ahead to the end of the year. I like to have financial plans that reconcile our biggest priorities & put them on a timeline. Of course, it's super hard to predict & build plans when the future is ever changing.

Here's how I've been roughly thinking about our financial priorities. Note that this assumes we'll continue to have zero non-mortgage debt, will maintain our existing retirement contributions (and will continue to grow to the IRS max each year, etc).

• 2016-2017
• Top priority - saving for a house in California. We're still sketching out what this will take, how much of a down payment we will need/want, etc. 
• Put *some* money in the boys college accounts. Maybe in the neighborhood of $2K, each year. 
• Travel. Continue with our existing travel budget & priorities.
• 2017 (April-September?)
• Top priority - buy a house. Our lease is over at the end of next August.
• Travel. Continue with our existing travel budget & priorities.

• 2017 (October-December)
• Rebuild savings, any repairs or furnishings for house, etc.
• 2018-2027
• Top priority - save $1,000/month for the boys college. This will put us roughly on schedule to have 85-90% funded for both. They will be responsible to work & save for the rest. 
• We will pay down all of our mortgages, on schedule. No plans to make the payoffs a #1 priority. For now.
• Travel. Continue with our existing travel budget & priorities.
• 2028+ (I will be 52, M will be 61)
• Pay off all mortgages
• Increase travel budget
• Retire - this will likely still mean working for enjoyment & flexible money, but not with the same requirements as we have now. It may also mean that we relocate to somewhere a lot more affordable. 

Obviously, my work plans will greatly impact our ability to do much of the above. I remain in a holding pattern. I know I will work at least until the summer of 2017. And, I get a large bonus in January of 2018 (assuming my employer continues this). I'm considering either January of 2018 or June of 2018 as my potential end dates. From there, I would look for more flexible work options, and will know exactly how much I'd need to earn to pay for our house, travel, college savings, etc.

What about you? Do you get anxious without a plan, even if it's rough? Do you enjoy running the numbers & seeing how things play out with your future? What are the big milestones you're currently tracking? We're in the "under 10 years" phase, where we have 9 more years until Nick is out of school, and then our world changes quite a bit. We will be paying for college (hopefully will have it funded by then), but won't have kids in the house & will have quite a bit of freedom to move around, explore new places, split our time between Washington, California, Hawaii? Tell me about your plans!