I am leaning toward dropping the price to sell it faster mainly because I don't want to kick the can down the road.

A good hoa provides amenities ,security , and increases property value through the maintenance of roads, landscaping etc. 

Please tell me you're sharing this because it's an EXCEPTIONALLY great deal, because I'm in the same area just starting out and if that's a standard deal I've got a long road ahead of me.

If you're light on the experience side, but are an accredited investor ($1M net worth or higher, or $200k / yr personal income), and want to be active in deals down the road, a good initial approach would be following @David Thompson's advice and participate in several apartment building syndication deals with your $500k.  

If looking for upscale residence, look in South Hill Village, Sewickley, McKnight Road, Baldwin, White Hall, Penn Hills,  and Monroeville.

I understand that building the business will be hard work, but this is the channel I want to use to build passive income down the road.

it's obviously not southie, but down the road, could be the next market to turn as everything else gets ridiculously expensive.  

One of our elementary schools back then was actually IN pennsylvania because it was just over stateline road on the west hill- that everyone knows is the best for sled riding!

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It also backs right up to a very busy part of antelope road and does not have a sound-retaining wall behind it (like the surround neighborhoods off antelope), but a standard wooden fence.