@Duke Giordano - You have done a good job in laying out the pros/cons of funds vs. individual passive investments. In a fund you are much more investing in the sponsor and his operating philosophy than the merits of the various projects within the fund. I have done both and have been more satisfied with the fund experience due to the risk mitigation. I now only invest in individual deals (debt or equity) when I have intimate knowledge of both the operator and the project. Even with top quality operators you can get a significant variance in performance from project to project. I see this in the quarterly reports issued by my best sponsors. For me, I am ok with passing up on the individual home runs to also avoid the strikeouts. The fund structure allows for this.
I am unfamiliar with exactly which operators would fall into the "smaller fund" category you mention. But, I would concentrate on the sponsors' experience/track record and the number of projects within the fund. For example, a fund with two or three properties seems to provide the worst of all worlds. Not enough diversification, but you get all the negatives of fund investing. Also, I see many newer sponsors "jumping into the syndication game" without a good track record and they frighten me. When I invest in a fund I want to benefit from the operator's experience, knowledge, and skills, and not pay for his education. As one example, there is a small sponsor who three years ago was promoting his single family rental fund in which he bought thirty thousand dollar SF homes, rehabbed them, and rented them. I didn't like the idea of investing in low cost SF homes in C/D areas in a fund with ten properties, so I passed. In a long phone conversation he was strongly selling the low price SF model, and basically told me I was wrong. Now I see the same sponsor exclusively doing MF value add projects in his funds. These MF investments are his first MF investments. This sponsor may eventually be very successful. But, I won't use my money to pay for his education. No thanks.