I quickly discovered the Bogleheads and FIRE communities and became an index fund investor three years ago, maxing IRAs and 401(k)s and all that fun tax optimization.

Consider trusts, LLCs , c-Corp, tenants in common, limited partnership, IRAs, 401ks, HSAs, maybe offshore entities, etc. 

think about Ira, 401k, HSA contributions to bring taxes down further.

While a Roth 401k can be transferred to other Roth qualified plans and Roth IRAs, a Roth IRA can only be transferred to another Roth IRA.

I already have a Roth IRA with stocks, and I know there's no good way to transfer that money out.

The IRA would own the LLC, but you could act as manager for the LLC and conduct the activities of the LLC. 

"TAX, LEGAL ISSUES, CONTRACTS, SELF-DIRECTED IRA" seems like a good start for BP categories.BTW - If you find someone who can address this issue competently pass along the name.

I recently discovered that as long as it is used for the direct purchase of a home and the account is at least 5 years old you can use up to $10,000 (without taxes or penalties) of a Roth IRA to help buy real estate.

I received a list from my SDIRA custodian of contacts that can correctly set up the IRA owned LLC.Any experience or comment on IRAvillage? 

@Mark GonzalezI'm Not a Finra business, but a lot of our clients are associated with FINRA and use their IRAs to invest in real estate.