But it is usually a less optimal solution. 

You had enough risk margin to absorb a loan that may not be optimal, and you have already learned a few lessons. 

Rent larger home, use cash to rent a smaller home/move to retirement community (disadvantage: less community of older folks; advantage is we can continue to own the home but make money off of the rent payments; but now we have to manage new renters)Basically asking if anyone has experience moving to a retirement community, and what the optimal move is with our current real estate assets.Where could we talk to similar people in this situation?

ARV about $180-195k My optimal strategy would be to rent it out to students $400 a room.

Are you planning on keeping the complex or flipping it once optimized? 

The best way to find them is to send out mailers.Some good lists to target are Absentee Owners with Equity, Seniors with Long-time Ownership and Homeowners with Low Financial Stability Scores.You can work with a list broker to optimize your list for your area.

Tax optimization is not a topic that many people like to discuss, but it can deliver equal value as other landlording tasks.

It really just comes down to if they meet the standards that you are looking for.Now if there is something wrong or sub optimal with their application, then that is a whole different story

Syndications will almost always be to cover the down payment, renovations, and other costs in order to increase rents and to optimize ROI.

I visit Oahu every year to check on my properties, optimize processes, meet fellow investors, and work on my tan ;)Besides my Oahu rental portfolio, I have invested in over 15 private placements/'syndications" passively over the last few years.