@Jason Hirko thanks for your reply. I agree it seems similar to a small scale fund or REIT but with a few key differences that might alleviate the SEC filing requirements and some of the other regulatory complications. Firstly, if members are given voting rights and major decisions such as buying and selling property or taking on debt are decided by vote while the managing member is responsible for the day to day administration of the business my understanding is that the interest in the LLC would not be considered a security. Second, an LLC or Series within a Series LLC in this model would only hold one property versus a portfolio of properties and potentially debt like a traditional REIT. This would tie the cash flow directly to rental income instead of issued dividends.
Let's assume for the moment that interest in the previous fictional example is not considered a security or that the business could meet one of the common exemptions of the SEC's Regulation D (504, 505, 506). Could this be a financially worthwhile endeavor? Or better yet, how would you tweak it to be worthwhile?
With rents at 1000, 1200, or 1500, allowing 50% for expenses and assuming a P&I payment of 400, monthly cash flow for Joe and Mike would be 10, 12, and 15, respectively, or 120, 144, and 180 annually...as @Jay Hinrichs points out, even with capital appreciation, not worth it.
If cashflow is allocated, not by ownership percentage, but equally among the three partners then cash flow increases to 400, 800, 1400 annually. Adding capital appreciation of 3%, Joe and Mike would make 7%, 11%, or 17% of their 10,000 while Bob would make the same plus principal reduction on the mortgage while getting his 20,000 down payment out for use in the next venture.
***I am a rank beginner at all this so please feel free to point out anything I am missing, calculation mistakes, false assumptions, or if I am totally of base.***