Keeping this as a rental would not cover the mortgage (we'd have to pay ~1500 a month including utilities) and we can afford the extra payment, but is it worth it when looking at appreciation?

There are some exceptions to this but this is the general rule.The $150,000 hurdle shrinks to $75,000 if you are married but filing a separate return.Creating an LLC does not suddenly bypass this.In actuality, you created another filing requirement which your CPA will charge you an extra cost for. 

As mentioned if the holding company is not solely holding or owning assets together funneling monies as a loan would further complicate if there is a default but also cause you to file extra tax returns = $...Yes you are taxed on interest income or any money that you make, does not matter how you structure it, what comes into play is not how much your taxed but how much you pay someone to figure out for you how much you need to pay and each layer is an added cost. 

I suggest going the extra mile by providing access to these services yourself, and you could even advertise features like $5 movie rentals on Prime Video to create additional value for your guests.Hope that helps, and good luck with your investment in Cancun!

I know the addage if you treat it like a hobby it will pay you like a hobby but if I have some extra cash maybe it's better spent on a 2nd home with the potential for income vs. just using that money in my primary home. 

The power differential is real and you are helping equalize the playing field  The reality is if you are an ethical and consistent strong performing syndicator/GP, you should be extra supportive of this.

He hit a gas line (not a huge amount of damage), and there is an extra bill coming to me from the gas company for the fix/labor/material costs.

But zero chance I would pay the extra to sell to this one buyer or expect debt to be forgiven. 

This approach requires more messaging though—and the impact of this at a larger scale could be a lot of extra work—but in our view, it was absolutely worth it.

Anyone with a little extra money on their hands with the intent of buying real estate may be considered a legitimate lead.