*NOT OFFICIAL TAX ADVICE*
It seems like you have a complex situation involving multiple properties and members within an LLC structure. Given the intricacies involved, it's wise to continue seeking professional advice to ensure you're making the right decisions for your investments and your specific circumstances. Below are some insights based on the information you've provided:
Self-Directed Roth IRA:
Setting up your individual portions of the LLC within a self-directed Roth IRA might be possible, but it's crucial to consider a few things:
Given the potential complexities and the importance of compliance, it's strongly recommended to consult with a financial advisor who specializes in self-directed IRAs and a tax professional before proceeding with this strategy.
Prohibited Transactions: Self-directed IRAs have strict rules about prohibited transactions, which include transactions that directly or indirectly benefit the IRA owner or disqualified persons (such as family members).
Unrelated Business Income Tax (UBIT): If the LLC generates income that doesn't qualify as passive income, such as rental income, your self-directed Roth IRA might be subject to UBIT. UBIT can erode the tax benefits of using a Roth IRA.
Complexity: Managing an IRA-owned LLC can be complex and requires strict adherence to IRS rules and regulations. It often involves higher administrative and legal costs.
Creating a New LLC in Maryland:
Creating a new LLC in Maryland to hold the properties there might offer some benefits in terms of segregation and potential liability protection. However, as you mentioned, the cost savings could be minimal if you're going to register it as a foreign entity in Maryland. The decision to create a new LLC should be weighed against the costs, administrative efforts, and potential legal/tax implications.
Leveraging Member Assets:
The strategy of leveraging a low maintenance account owned by a member to fund the real estate LLC can work, but it's essential to have clear and legally binding loan agreements in place between the individual member's personal LLC and the real estate LLC. These agreements should outline repayment terms, interest rates (if applicable), and other relevant terms.
Tax Considerations and Structuring:
When dealing with multi-state properties and a complex LLC structure, tax considerations can become intricate. Different states have varying tax laws, and the choice of LLC structure can impact tax obligations. Engaging with both a CPA and an attorney who are experienced in real estate and multi-state taxation is highly recommended.
Given the unique and intricate nature of your situation, personalized professional advice will be invaluable. Collaborating with experts who can provide specific guidance based on your goals, risk tolerance, and the current regulatory landscape will help you make well-informed decisions. Always remember that the potential benefits of optimizing your structure should be balanced against the administrative complexities and potential legal and tax risks involved.