@Andrew Reyes and @Basit Siddiqi mentioned various factors of why this is happening, and the short version is: it is weird and confusing, thanks to our overly complicated tax laws. 

As he mentioned you ABSOLUTELY should discuss this with your broker.

The owner mentioned some replacements and maintenance he has done over the years. 

What happened with that plan you mentioned at the end?

The video mentions a list of expenses to consider but for the quick analysis the 50% rule seems like  a good rule of thumb.https://www.youtube.com/watch?

I personally don't understand how anyone can start out wholesaling for exactly the reasons you mentioned.

As I mentioned, the condo association docs don't prohibit it, but they still may try to block it and get lawyers involved.

As mentioned, I don't have much to offer in terms of real estate experience but I can certainly keep you in great coffee and humorous travel anecdotes for your time if that means anything.  

I saw criteria for this before that mentioned you can't have lower pricing on another platform than on HA/VRBO, not sure if this is still criteria.Thoughts?

@Jay HinrichsAlways feel honored when mentioned by name from you.