Looking to do a deep dive into HOA's of potential condos I plan on purchasing in So.

There can always be potential tax issues when debt is moving around due to changes in debt basis.  

Either way, I would engage the services of a tax professional as you do need someone to help you maintain your books if you haven't done so. 

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Hand-in-hand with number 3, you get to leverage favorable financing terms by putting a very small amount of money down (compared to non-owner occupied financing) which in turn makes your investment pretty small, but potential return on that investment very large by percentage.

Having it sit on the market for months like this could potentially drain me, financially.

I think the responses that you will get will probably range from "scale faster and put down 20% on multiple properties" to something akin to a Dave-Ramsey-mindset.When it comes to investing, personally, the route that I see as potentially safer when it comes to cash-flow is the diversification of owning multiple properties.

Seems like there is a lot of potential!

I would suggest visiting Baltimore yourself to determine its potential.

Have you found yourself looking at other markets or are you seeing potential in Dover?