Jimmy - I like you already... Great question #2!
HOA - I have seen good, bad, and really ugly. I have been on at least four different boards, though I am not currently on one (Praise God!)
I think the best way to see the difference is to go to neighborhoods with HOA's, and then drive a few that do not have HOA's. While there are always exceptions to the rule, many neighborhoods without someone overseeing the adherance to the declarations and bylaws show decline in maintenance and curb appeal. Where an HOA can enforce the rules of parking, yard care, paint colors, etc... without an HOA, you could end up living next door to a home painted the colors of Superman, as a friend of mine in the North Central has found themselves. Truly, the home looks ridiculous, but the owner thinks it looks good... An effective HOA helps maintain the value of the neighborhood.
My neighborhood, Rogers Ranch, for instance, is one of the few neighborhoods in San Antonio that has actually gone up in square foot prices over the last few years, while literally 98% of all other neighborhoods have seen some measure of decline. I personally attribute that, at least in some measure, to the effective and reasonable HOA leadership.
On the other hand, there are those types of HOA's that are similar to the Gestapo... yeah.. not so fun. But, even then, in the long run, they are helping the neighborhood maintain its value and desirability.
That's all I have to say about that!