And it's actually pretty flexible (other than some timing and documentation issues).  

What would be some common pitfalls in either transaction?

While it works like a charm with Airbnb I have a really hard time getting it to work with VRBO.Has anyone had a similar issue?

They also manage the property for you and deal with tenant issues awards.

I have found in my limited experience that I can work through the other issues, if the PM is doing their job and keeping their units occupied most of the time at market rents. 

It sounds as if the property is owned as tenants in common where the property is deeded to two different LLC's.If this is true, you would report your 50% activity on your individual return if it is a disregarded entity, or on a partnership return if your LLC has more than 1 member in a non-community property state.Best of luck.

In essence, less than 20% (of the commonly-held-average) ARV is a slim margin, and you should justify it according to your experience and comfort.

Your post is confusing because an HOA cannot make a modification to a common element and then charge 1 owner for that *UNLESS* that owner or their tenants damaged the property to begin with.

That's basically common knowledge.

@Ramsin Jacob you should be able to do this no issue.