Given that your governing documents state HOA liens are junior to mortgages, it further complicates their claim, as they may not have the right to impose a super lien in this instance.

As mentioned if the holding company is not solely holding or owning assets together funneling monies as a loan would further complicate if there is a default but also cause you to file extra tax returns = $...Yes you are taxed on interest income or any money that you make, does not matter how you structure it, what comes into play is not how much your taxed but how much you pay someone to figure out for you how much you need to pay and each layer is an added cost. 

I’ve had clients pay $100k for a sewer line though (commercial properties, complicated lines running under parking lots, sidewalks, landscaping and the bid includes replacing the landscaping too, etc. or requiring a permit from the city to close off the road for the day with traffic control, etc.).

It can be tricky managing properties in East Cleveland, but I don't think it's that much different than managing properties in C and D neighborhoods, it's just a bit more tricky with getting contractors over there, but I'm working on a listing in East Cleveland and had a contractor do a bunch of work on the property and didn't have any issues.Another issue with East Cleveland is they have point of sales, but Cleveland is going to start doing that soon, but definitely adds unnecessary costs when margins are everything.  

Right now I only have three properties that all rent for approx the same amount so it's easier for me but I worry once I'm at 4 or 5 it's going to get a bit complicated.

If your going the CC wrote, which Crum you just made it sound very complicated (moving parts to pay a bill), might as well get the three CC's and the max limit you can. 

More unnecessary damage.

Improvement exchanges are really complicated, and in my view unnecessarily risky for this type of asset.

Easy fix but they like to make it more complicated and more expensive so that they make more money.

I am not sure I will go through with it due to it bing a bit complicated and you never know with a buyer not being able to seal the deal a year or two later.