The DSA is radical for my tastes but I found it funny how you framed that comparison. Like that's the only negative thing about Trump that people are weighing when deciding not to vote for him/those he endorses.
FYI there's no 10% penalty on Roth conversions but you're right that you need to have outside cash to cover your taxes. I've had clients get caught because they took out $100k, withheld $20k in taxes with only $80k going into the Roth. There is a 10% penalty on the $20k that did not go into...
That's a sound strategy that a lot of my clients are doing. I wouldn't worry about the 5 year rule too much, IMO your Roth should be the last place you pull funds from anyways.
As far as using a financial advisor, I personally use one for about half my portfolio. I do it because I get a ton...
FYI a backdoor Roth and Roth conversions are two separate things.
You can do a Roth conversion at anytime and whatever amount is converted from your 401k/Traditional IRA adds to that year's taxable ordinary income.
A backdoor Roth is where you make a non-deductible Traditional IRA...