Quote from @Marlena Hawkins: Does anyone know what insurance (liability, E&O etc.) is required for Property Management companies in DC and Maryland? 

It's about avoiding speculation and focusing on fundamentals.Why I think is it so powerful?

Do to the state mandates that require 100% reserves in all categories, combined with the rising cost of their neighborhood insurance policy, my strong recommendation is you find out what further anticipated spikes in association dues & if any possible special assessments are looming.

I know there is not a ton of resources that don't require large financial commitments, just wanted to see if anybody knew of cheaper alternatives. 

Or putting 20% down in a conventional loan so you can also avoid PMI. 

Then add any other codes required where you want to build and study those as well.

It does take 1-2 weeks to accomplish, so does require some effort and monitoring on your part, but sounds like you are a diligent self-money manager, so should be easy for you to accomplish. 

Some areas allow commercially zoned properties to share one large septic system (think sandmound or gravel type system) or would they require an individual on-lot septic? 

Do you mean it would need an architect because that's required by the jurisdiction, or because the project itself would need an architect's expertise?

Unless you suddenly become a stellar STR Host and property (requiring additional spending), why not sell and make some better financial decisions....