I'll live off my dividends [hoping to get it to $1k/month] from my taxable account first (since they are already taxed, I'll use them). I then plan to rollover about $30k/year from 401k to roth ira. At which point, if I need more money I'll take it out of roth ira. If I need more than the 40k (rollover+dividend), I'll sell my stocks in my taxable account. All money is today dollars, not sure what inflation will do to this part of my plan :D
I know this isn't very tax efficient but I need a way to roll money from 401k to roth. I suppose I could just do a roth 401k but I gain more from a 401k at the moment.
When I hit 50, I'll draw on a small foreign annuity that grandparents bought for me (everyone in family has one, it was like a "being born" present, I'll also "reinvest" part of it into the next generation of family members), at 60 I'll draw on a pension (won't be large since I plan to be retired by 45 so won't have too many years into it, 15 years?), at 70 I'll draw on social security. And by the time 70 hits, I hope I will have most/all of the money out of the 401k and into roth or else the minimum distributions will be taxed a bunch.
this will all be in the future though, to get to the point of $1k/month dividends, I need to work another 15-20 years. I could always just give up on this number and go early, but while I enjoy my job I see no reason to "rush" it. It'll happen when I get tired of working I suppose but until then , it's just all plans and planning.