Denver, I think you've thought it all out very well and have several great plans/options to choose from. You don't come off as thick-headed at all, there's just a lot of complexity in all the rules, tax considerations, and built-in ambiguity in not being able to predict the future with any certainty. I've been over it myself many times in the same way trying to figure out how to balance the "two retirements."
Honestly, I don't think you can go wrong with any of your scenarios, which is a great place to be in! They can all work with various pros/cons that you're already noted.
Personally, I would continue to max out the 401k/IRA and Roth IRA contributions to take advantage of the tax deductions at least for the next couple of years. The net effect is you'll be saving up even more, courtesy of the government's tax policy. You could always ramp it down after a few more years. But you could absolutely and reasonably decide not to do that and instead focus on saving up more free-and-clear money for age 40 - 60.
I'm not particularly bothered by having a bunch of my 'stache tied up in 401k/IRA because I'm comfortable with the various methods for withdrawing early at no penalty. But it does take some extra effort, so it could make sense not to do that if you're not so inclined.
I will add one thing: I don't know your real estate market, but I'm very bullish in general on owning at least one rental/investment property if your market is favorable. Owning real estate offers several big advantages -- it positions you for a nice income stream, generally appreciates in the long run (YMMV), gives substantial tax benefits, and is a great hedge against inflation. So if you're up for it, I would direct some of that investing towards an investment property following some of the excellent advice of users on this forum (Arebelspy and Another Reader immediately pop up in my mind). In 10+ years of owning a rental property, you could be looking at a very nice cash-producing asset for your retirement that also provides you with leverage and a built-in place to live should you ever want/need it in your later years.
While most prudent real estate investors don't rely on appreciation, many find that it ends up significantly boosting their net worth in a good market, in a way that surpasses anything you could ever do in the stock market or elsewhere. Leverage is amazing, and in many places there has never been a better time to buy. As an example, if you invest $50,000 into a $250,000 property that appreciates, on average, 4% over the next 10 years, you will get huge gains (value of $370,000 after 10 years, or a net increase of $120,000). It is not your $50,000 that is growing at 4% per year, but $250,000 growing at 4% per year. And at the same time, you get an income stream, increased equity by paying principal, rents that go up with inflation, plus tax write-offs.