The fact that he doesn't do well without a prompter tells me that he doesn't rehearse enough.

For example, if you have 3 very quiet tenants and rent the 4th unit to a rock and roll band drummer that says he rehearses (alot), then you probably are asking for issues.

You have to "practise, drill, rehearse".

Your disposition reminds me of an analogy from some military experience: Let's just say I was a warrior in the US military and had some close encounters with not so friendly folks, we trained for a multitude of scenarios constantly, rehearsed over and over, ran drills for various tasks, planned and analyzed, and even agreed on what specific preparations would be made as well as form a consensus on how to strategically maneuver and react to the mission ahead, we over-prepared often, almost to a frustrating level; nearly every single mission we conducted (99%) all the planning and preparation was seemingly useless, as soon as any action stimulus began, chaos ensued, what I like to call organized chaos on our teams part, yet it wasn't the planning and strategic efforts made prior to the mission that enabled us, we always worked through the chaos with the fundamentals, the core efficiencies we had learned and trained, it didn't matter what rehearsal and plan we chose, it was the fundamentals that afforded us the opportunity to weather the chaos and react proficiently.

Background: a couple years ago my brother had his wedding rehearsal dinner at a winery near my mom's house.

I think the odds are against a single small time investor with littlE staying power. now going into a syndication it is a formal rehearsed plan: the costs and problems have been researched, there is experienced project mgr hired and even lawyers on standby to protect the project, property managers ready to reminder, collect , evict tenants rightfully and plumbers, electricians, trades mens will all go to a syndicated project any day than a small time landlord to do business. 

We are also planning to target the large number of wedding parties that come through Charlottesville and surrounding areas, the main house would be great for rehearsal dinners etc. 

This business is complex in every aspect, and has been known to leave even the most rehearsed of us on our backsides asking... wtf just happened? 

It's far from professional, and not at all rehearsed, so keep your expectations low

So, I rehearsed and rehearsed what I'd say over and over and it got me even more nervous.