@Carl Fischer
It is not a large sum, I only have about $80k right now, but that could go a long way right now toward investing in more real estate to generate income today. It is in a company sponsored 401k, and I've contributed to it from day 1 since I was 22 to get the max company match. It was started whether I wanted it or not, and it was good to have it and I recognized that, but now it is very hard to resolve not having access to money I've invested and that has grown simply because I'm not of a certain age. I've already taken a loan against it to get started in real estate and that has gone well thus far, outpacing the market over the same time.
Besides even being cumbersome w/ all the rules and regulations and causing missed opportunities, I think the tax deferment I'd be giving up is also diminished by the fact that real estate held in a self-directed IRA does not get the benefit of depreciation nor can you do a 1031 exchange. Both depreciation and the 1031 exchange with today's money, in my opinion, kind of level the playing field of tax deferment for future money.
The tax deferment benefit in my case I do not think is great enough to win out. Since I am still "young" I still hopefully have a lot of time left. I agree with your comment to make money in and outside of an IRA. A traditional IRA or 401k plan though are not the best for me because of this time remaining. The direction I'm going and the life plan I have, I should be in a much higher tax bracket than where I'm at now. So a Roth would make the most sense (and I have one started already for the day I have residual income to start socking away again). If I can grow money tax-free for the next 30yr and only pay tax on $80k now instead of on some millions (hopefully) later, that should be a far greater benefit to me. It also provides the flexibility to access the funds invested should the need or want ever arise to do so instead of it all being locked away.
This is my perspective based on my situation. I consider myself not the typical millennial, but try not to give up on our generation yet! Thank you for your time and input to my question!