The first place was probably the worst place I have seen yet in that it would need major remodeling to be a proper 4-plex.

Here's one example - check the average life expectancy column: Life Expectancy of Appliances The HOA could actually be a good thing if run properly, at the expense of some control.

If you have window units and/or zonelines, they're not going to condition the house as well as a properly sized central gas system with correct number and location of vents and returns.

Assuming the list is properly filtered, is this enough to smoke out the first deal?

That is not such a bad thing....forcing us to do proper DD.  

Now the area feels very safe, and very hip hipster bars are popping up along 14th street, heading north from Columbia Heights proper.

Yes, you need this information to properly screen them. 

Before you send them out make sure the property mgr sends a notice with the proper lead time so the tenant has no choice but to let them in.

Most of your problem looks like the posts were not properly set in the ground. 

But my main concern is understanding The HUD Home Store, how to bid properly, understand what is expected of me (besides paying for it) If I can get PreQualified here in Washington State to purchase a home lets say in Missiori for instance or Montana.