but maybe a lower end condo for a staright up rental on another Island would be appropriate.

Be that specific.Estimate maint and repairs appropriately to higher churn/turnover markets and property types vs just raising the vacancy rate. 

Furthermore, the condo cannot be rented because there is a 15% thresh hold for rentals which is currently already met.Questions: 1) What appropriate steps should be taken to expedite HOA responsiveness so the sale can quickly proceed? 

But you and your son can adjust the tenancy however you want after the 1031 is over as appropriate. 

From an investor standpoint, two ways: You can work with an investor-friendly attorney to draw a contract up for you or you can use the standard TREC realtor's agreement and add any special provisions to it in the appropriate area of the contract.

@Andrew Smith, I am not sure if you are asking about the federal credit to rehabilitate some of specified properties in certain zones or certain year old. 

@Simpy CheemaHow you found the property will indicate how they will prefer to be contacted.If you found the property on the MLS - you will likely need to go through the channels of communicating through real estate agents.If you found the property through a website(Zillow or Trulia) and it is FSBO - they likely left an appropriate method to communicate.If you found the property through a website(Zillow or Trulia) and it is through an agent.

If you and your spouse were the taxpayer on the relinquished property, you also need to be the taxpayer on the replacement property.Here's an online article I found with some info about the debt replacement requirements:http://www.aptmags.com/blog/1505/1031-exchange-debt-replacement-requirements.htmlMay I strongly suggest you talk to a real estate tax attorney, or knowledgeable CPA in your area and get appropriate guidance.The last thing you want to have happen is a defective 1031 exchange.

Instead of looking up and writing out there 4 first names in every email, when they email me and when I email them do you think its appropriate for me to simply open with: Hi Ladies, Email content...I don't want there to be any potential for that greeting to appear sexist or overly friendly or anything like that. 

Work with a real estate broker to find out more information and come up with an appropriate plan of action.