I'm not in favor of the mortgage broker if your situation isn't complicated where you need their services and pay the broker fees. 

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.

Also, be sure to consult a CPA about the timing of transitioning properties to an LLC to avoid potential complications with financing or taxes.Take time to compare multiple lenders and products that fit your strategy.

In the 2010s we did the BRRRR thing not even knowing that the acronym existed and now we're are in a good, but complicated situation.- The commercial mortgages (all under 5%) are going to start being paid off in the next 1-5 years.  

The reason I do this complicated interview process is because you want someone that knows what they are doing.

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.

To make it more complicated, I have ACV insurance, so that makes it harder.

They do hundreds of transactions a month and can guide you better than most attorneys when it comes to title issues.They use a complicated form that creates extra work and confusion with no benefit to the buyer or the seller. 

will i also have to furnish proof for those items complicating things?

Yes, having two liens can complicate things, especially with a conventional lender.