And she says that most of her Section-8 renter never move out, which means she doesn't have to continually have to be assessing new prospects to be renters, which can take up a lot of wasted time, as well as lost money, of empty Rentals, while waiting for high-paying qualified renters to appear.

This means in order to avoid paying rent, being assessed late fees, or being served with eviction notice, you have to notify the landlord in writing or verbally of your economic impact and do so within a certain timeframe.

Would all real estate holdings be given an assessment at year-end?

I looked in the city records and they assess the property for 500k but the owner is asking 550k.

If you want a software to collect dues and assessments, provide reports to the board, communicate with members easily individually or en mass, I recommend Smart Property Systems.

When (if ever) was their last special assessment? 

We will have a couple waterproofing specialists to assess the issue but my agent said for sure they would recommend doing a drain. 

Additionally you need to assess the odds the tenant stays and will renew the option.

Underfunded HOA's mean special assessments and they can kill your cashflow the same way not having proper capex budgets can.

You want to check out the condo fees, how much they have changed over the years, were there any special assessments and what are the condo financials and rules.