The nice thing is I can get a judgement and after a month get a lien.

The HOA got to keep all the proceeds (up to the amount of their judgement) and unfortunately the remainder to the owner. 

You will have to then make the judgement call how to proceed. 

We put deliberate effort into this, from remodeling to not raining rents, the cost of a turnover is just too high.

Don't be afraid to follow through the process of eviction and seeking a judgement for unpaid rent and damages.

Plus here the schools closed the last three days of this week  because of the rain and 3 days last week from flu/too many people out sick, so not much is getting done anywhere.Also, they will be working Saturday too, which they generally do not. 

That means they claim the property  has defects and instead of getting a judgement court is stalled another month sometimes more during which time a city inspector will do an inspection of the property. 

We then had a roof inspector come out who said that the roof has to be replaced within no more than 5 years but is probably already leaking in a few spots (there hasn’t been any rain lately so he can’t find any confirmed leaks but those were his thoughts.) the cost for the new roof is $7K.

I would threaten court action and the impending doom of a judgement of fees + court costs coming down on them before actually going to court. 

Then the rainy season came (he was also a new owner) and rain was coming in through his light fixtures.