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

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

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.

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

I remember a couple years ago they ran a Superbowl ad and were followed up with a large gain in market share...let's see what this does, but it sure won't hurt them.

I have a few clients doing pretty well up there.There are a handful of DSCR lenders that will do loans of under 75k, but if you have a few of them and they are close, it might not hurt to look into some smaller portfolio lenders as well if it comes down to it.. 

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.