However, my wife took advantage of an impromptu conversation and it looks like they will stay until January. 

The exact amount of capital gains you can offset will depend on the cost segregation study results, so it’s crucial to discuss this with your tax advisor to ensure you’re maximizing your benefits while staying compliant.

The goal is to make them stay for a long time.  

They are both in demand, and appear to be growing, like multifamily.I would stay away from office and nota big fan of retail strip centers. 

I have this tenant who has been staying on the property for last 8 years.

My oldest daughter will be at kindergarten age around the time we would be moving.Do you plan on repeating the process or are you going to stay put for the long haul?

I had a busted sewer pipe in there, which has been repaired and everything has dried up, and appears to be staying dry.

On the other hand, I would like to hear some recommendations on sites to manage the different postings on different platforms, again I am a beginner with only one villa, so I would like to stay on the $20-$40 a month. 

Managing or leasing the property yourself would likely be considered self-dealing, which is prohibited.To stay compliant, it is best to hire an unrelated third party to handle the leasing and management duties.

I prefer to stay on the boat but totally understand the sentiment.