Oat,
Have wanted to reply to this for awhile, but was on vacation and work, etc...but anyway.
In your very first post you write: "
Just enough to never have to go to a job again out of obligation".
About 4-5 years ago, I was in the exact same boat....did a bunch of reading of various blogs, books, etc and
posts in here. Here's what I did (at 3 very high level steps)...there's a lot involved in each of these. But if I can make one overarching statement, it's "live way below your means".
Step One - The Goal/Plan
The most important thing IMO is to lay out a final goal and get Mrs. Otis to be aligned with whatever the goal is. This will by far be the biggest hurdle. From there, start mapping out a plan...again, alignment is key. Expect arguments, fights, negotiating, etc.
Step Two - Eliminate Debt
The biggest first step in this plan is to commit to paying off all of your debt ASAP. If you look at the core of the definition of "debt", it's you owing something to someone. If you have none of this, you're on your own terms. Now I realize you're getting ready to get a house at double the mortgage, so you're already behind the 8-ball there.
Now typically when I mention this, I'll have a bunch of people start attacking me....."why would you pay off debt at 4% when you can get 7-8% returns in the market"...yada yada yada. In short, my answers are "Freedom, Security, removing my biggest single monthly payment for the rest of my life". As I'm only 6 months away from this happening, it's absolutely liberating knowing how much free cash I'll have every year to literally do whatever I want with (add more to retirement, invest in businesses, real estate, travel, etc).
FWIW, I was putting 35% of my take home salary towards paying off debt. (i.e. I live way below my means)
Step Three - Figure out minimum costs you need to live
This is obviously different for everyone, but once you've eliminated debt, you can probably get a good idea of what you need to live off of. Also, this # goes down once kids are out of the house. From there, work backwards, and that will tell you what sort of income you need to retain to keep the lifestyle that you want. Then, you can figure out how to obtain that income however you wish.
It's that easy!
You're a smart guy, I don't think I'm telling you anything that you probably don't already know; but I could be wrong here, but I imagine that you're the type of guy that needs to see it laid out in black and white by people who have done what you want to do. I'm like that alot.
It's an absolute amazing feeling knowing that I basically have all of these different options in front of me.