That is a safe harbor from the IRS with a couple of caveats. 

Over the years, however, we’ve found that we end up coming down to Orlando quite a lot, especially in the last couple of years, and we end up staying in vacation rentals (Reunion, Championsgate, Storey Lake typically).I would love to simply pull equity from the current property but given that it’s a long term rental and we are Canadians, from what we understand it’s not an option for us.we love reunion but I feel that would probably not be the best for ROI.  

The GC is likely at least a couple of more thousand dollars.  

If I had to choose a couple to look into first, it would be House Hacking, Mid-Term Rental, Short-Term Rental, and BRRRR.

My partner and I have a couple units we manage as well in Washington DC.

@Loren Souers Couple of questions. 

You could ask the Contr to use a flexible compound if this happens again, or maybe even now...https://www.dap.com/products-projects/product-categories/pat...Take pictures of every place it occured....it's easy to forget after a couple years....

It seems like PSI has grown, a couple landscape companies that way either sold or partnered with PSI because these landscape companies no longer do snow removal and refer people to PSI.  

If a tenant buyer does not exercise the option within the three year period of time, then we can do a couple of things.1. let's say they leave early.

Assuming you could take out a couple 100k you would have the buying power to start a cash recycling business (brrring or flipping).