We voted down a special assessment of $2,500 for painting back in October and a $100 increase in dues for painting in December, but the board has just sent notice of another meeting to be held in March for a vote of a $2,350 special assessment. 

That is very impressive, specially given that this is your first deal.

The presentation was put on by an attorney that specializes in this exact transaction. 

I’m looking for recommendations for a small business/real estate attorney and CPA. they don’t have to specifically specialize in real estate.

I wanted to clear a few things in case It happens again.In a deal like this, how do you guys deal with the HOA, meaning, do you investigate about active/potential special assessments?

It's about the owner, not the service/product or customer.

You would not doubt stay involved for the comfort level your friend has with you but there are a wide variety of nuances with any commercial lease that would dictate the need for someone who specializes in the product type.

I'm a investor/realtor based on the Central Coast and I specialize in Multifamily and other investment type properties.

It is a harder product to find but try using the verbiage of "LINE OF CREDIT" on an investment property rather than HELOC. 

You should be able to product rent rolls for the last 2-5 years documenting your vacancy rate.