Special assessment had to be made to pay them which ran six months behind.

You could also have provided other documents to help a buyer assess the potential financials of the deal.You are always in control of what YOU do, and NEVER in control of what others do.

@Susan TanYou also need to find out what special assessments they have charged in recent history and what the financial health of the HOA budget looks like.

It was a normal day for me browsing the MLS when i ran across a beautiful 6-plex....For my first investment property I am looking to owner occupy ( house-hack ) a Multifamily property with a 0% down VA home loan.I understand this isn't a residential property but Is there loans compatible with a commercial property such as this 6-plex?

When the tenant gives you the "official" notice, ask for a look-see to assess how much you need to do and start advertising it as soon as you can with the caveat it'll be available 1 XXX 2020. 

I agree central a/c is the way to go.But you will need the a/c condenser, a pad (or suspend it on brackets), evap coil, line set, electrical circuit & disconnect so you're probably looking at closer to $2500-$3000  using compatible Goodman parts & depending on what they charge to install it, (usually around $800-$1000).

Both the assessed value & market values indicated on the county website seem unusually high to me.

It is quite difficult to assess what you should do without knowing your goals, so I'd recommend getting as overarching about that as possible, and then getting granular.It seems like you might have a favorable tax-basis situation with the NYC home (obviously verify all of this with the right competent professionals . . . i.e. not me). 

Technically I believe it is the assessment that is actually being appealed.I will ask around and let you know what I come up with

I'll give you an example, I live in a condo personally, and after my 1st year they raised my fee by $50 per month, gave me a $6 000 special assessment for a new roof/siding that needed repaid over 3 years, and they just now stopped allowing anyone from renting their units.