I've been communicating with the tenant over the past few months to try and get them to set-up a payment plan and have had two letters sent from my lawyer outlining what is owed.  

I have all the necessary letters, documents photos etc that show they are responsible for the total cost - responsible for the misdirected water - plus harassment & smoke screens  Lawyers I have asked have either waved it away as easy, or told me 'you can never win against a HOA'   Neither angle has been helpful not explained to me. 

Or should I leave it up to a lawyer at the closing? 

Hi Sarah,I'm a real  estate lawyer here in Santa Cruz.

I shouldn't assume you wouldn't want to live out here but actually one of our tenants was a lawyer in LA and came back to where he grew up. 

The more I can help the project the higher my paycheck at the end of the tunnel.In the end, each of us will have to have a certain comfort level with whomever we hire whether it be our receptionist, our CPA, our lawyers, our lenders, our Realtors, and yes even our mentors.

First off, I am not a lawyer, blah blah blah.

Whether it's contractors, lawyers, suppliers or partners, I always try to meet with and communicate with these people several different times before agreeing to do business with them. .

My goals are to purchase a single here in Boston, build a team near CT or Springfield Ma made of contractors, a lawyer and a handy man. 

We help produce a business plan for a potential business and then made a recommendation on whether or not they should go ahead based on that plan.Other areas you can look to for help are potential Professionals you will need (Accountants, Lawyers, Insurance Agents, Suppliers, etc.)