I don't enjoy nurturing and closing sellers on a regular basis.

Now granted that has gone off the rails because I have decided to change our focus because my end goals changed, but doing the exercise helps create the path to walk and figure out what the next steps are.

I would also advise that you keep an emergency stash of cash in your regular bank.

They are regularly getting poor valuations compared to the cost to add the ADU.   

From there it's your regular ol' cash on cash return calculations!

The winning bidder gets the right to possession, but usually cannot exercise DIY possession.

Would you still use your friend as your GC and just pay him his regular rate (and would they be happy about the new arrangement)?

I don't know but I have plenty of Canadian and American friends and acquaintances who travel (regularly) to Mexico and the Dominican Republic but I don't actually know anybody who has vacation in Puerto Rico (unless they haven't told me of course).As can be expected, the most profitable form of real estate investment in the region is short-term rentals.

And he knows who's working regularly, who's only off-and-on, who's going through troubles, who needs extra work.

I'm interested in doing that for a property we just renovated and I'm curious on how to proceed, especially if the tenant decides to exercise their right to buy.THanks