@Kevin Si the main point I heard is that you're approaching "retirement" not active management :)You can partner with proven operators who can effectively spread that 1M across 1,000+ Multifamily Units with less downside risk WHILE you keep your retirement TIME.

Some believe that is the biggest problem with low numbers and hosts feeling like STR is a dying strategy, they never did understand the market they were buying into.

If I'm wrong, there's no downside.

I think that's the biggest question... and yes, you can find renters to live in a place that won't well, so a property like yours may not sell for market value, but it could rent for market value.

Perhaps the biggest reason of all: Housing pricing have been on the decline for 8 years (national averages) and many would-be buyers are afraid that prices are going to continue moving down.

Biggest issue is that 2 of the buildings have history of flooding.

When I first started, I thought the brand made the difference, so I picked the agency that had the biggest brand in the area.  

The downside is you have to "refresh" them daily which takes 2-3 minutes every morning. 

I read in Money Magazine that one of the biggest mistakes investors make it paying the typical fees to investment brokers, so I am looking to get out of that but don't want to lose my tail either.

The biggest turnoff I experienced when interviewing brokers, was how many of them just expected you to hammer your own personal sphere, bugging them to refer you or sell/buy with you as a newbie.