What is the current assessed value?

I asked: what his situation was (to assess motivation)last time he visited the property.when were there last repairs done/ what repairs are needed (he says none, the properties passed inspection to rent.

It could also maybe a cost for some type of assessment.. 

I don't think that your assessment is really that high.

Does the HOA have enough in savings to cover these expenses or will they have to do a special assessment?  

These bills seek to cap the fees that community association management companies may charge a seller to provide information about their association dues, fees and assessments prior to closing.

So if market rent is $100 higher, increase rent $50.The main thing is to make forward progress and to feel good about it.  

Might have led to assessments to all owners to cover needed repairs.

I noticed there are special assessments on the property for 1500$ for unpaid citations also so that's indicative of someone who is flat broke.  

But I would still call it a work in progress.