HOA is currently $172/month, with and additional $44 for club fees, covering club amenities, including a gym, boat lift, a restaurant etc. 

Also, the fees plus being a forced buyer with a deadline on a 1031 exchange may negate the small tax savings.

Maintenance costs are a huge factor in the profitability, or not of any investment property. 

I dont know your business model exactly but I assume you collect some referral fee from the supplier?

However, if that effort fails, the local agent is equally liable – criminally and civilly – for any fees, fines, etc. associated with the property." 

Enter recurring charges and automatic late fees.

Have you considered a flat fee MLS listing as a way to gauge interest and possibly sell?

HOA fees, in particular, seem to be the biggest hurdle.

This focus gives you a national reach, and that oh-so-important factor; scalability. 

The problem with selling is a lot of that equity will be lost when you sell it either through taxes or payments to your listing agent.If you ever have the ability to limit these types of fees and still be able to use your equity to fund additional purchases I think you should.