All this vigorous energy oozing out of my essence and there I was; splattering it around everything like a three year old kid frolicking around in a muddy rain puddle!

Isaac Braun you are owed rent until it is RE rented plus any damages (security deposit - Paint, flooring, etc) plus RE-leasing fee or lease termination fee if it’s in your contract.Most highly qualified people won’t stop paying rent, forcing you to evict them and get a $$ judgement messing up their credit.

Every time it rains the basement flooded because he did not properly install a drain outside.

I'm thinking no redemption for HOA judgement, but not sure about that. 

The buyers inspectors literally praised the work we had done throughout, but a week ago the CL-100 wood infestation inspection came back noting a small bit of non-structural exterior sheathing damage along the bottom of the back wall behind the vinyl siding due to moisture :( The good news is we are 99.9% sure the issue was caused by rain water coming off of the roof and landing in an area that had standing water before we brought in some dirt and gravel to resolve the drainage issue during the remodel (townhouse is on a slab). 

Hello BP, I bought a SFH in 2017 and during the closing period, there was some water leaking into the garage after a rain.

I feel I wont be using biggerpockets again from all the doubt and harsh judgement with very minimal actual advice.

Those who say it is the "perfect" time would make me question their judgement.  

Is there a possibility of structural damage ( stud rotting) due to rain pouring in through hole in roof?

For example, when you close at a title company, they are the ones who will check for liens and judgements on the person AND the property.