Now, these sound more like questions that are worthy of getting professional help: strategy, direction, long-term projections, etc. I would have no problem if you said "I'd like to engage a (fee-only) financial planner and/or tax planner to determine how to structure my portfolio for future goals, given that our incomes are rising, we have a number of investment accounts, and we have in mind to retire in XY years. We would like to build our portfolio and lay out a distribution strategy, including understanding the sensitivity of this strategy to potential significant costs (e.g. healthcare) and tax changes."
Go for it! But I'm thinking you now want a CFP more than a CPA.
In terms of direct answers, Roth has a distinct advantage in terms of taxation on earnings, but there are caveats. if you wanted to pick something particularly risky, like individual stocks, then you have to understand that you won't be able to take capital losses from the account, and understand what that means to you. And, of course, there are all the questions around access prior to 59.5 years, and how you feel about that.
To your comment on cheating the system, does it make you feel any different if you knew that this was left in the law *intentionally*? The tax reform act of 2018 made a number of changes to IRA's; this method existed beforehand, and does again now. So, it's not that it's a secret. Moreover, a complex tax system will have many boundary conditions: some work to reduce taxes, some show >100% taxes on small increases in income. Cheating is making up numbers or doing something to change the math. Hacking is understanding the structure as the numbers as they are, and making optimal choices with that knowledge. Certainly, there is plenty of discussion here on the ACA cliff and managing around that; does such talk also give you similar feelings?