Suppose I fund an LLC with 100k and my partner provides sweat equity, so we each own 50% of the LLC. Suppose this LLC has a single activity, a rental house bought by my 100k and worked on with that sweat equity, resulting in the LLC owning a house with a 100k depreciable basis but with a market value of 200k (ignore nondepreciability of land for simplicity). Now, 366 days later, I pay my partner 100k for his shares. What happens when the LLC becomes a disreguarded entity?
If my basis in the house now jumps to 200k, that would make sense, but a basis in LLC shares automatically converting to a basis in the property owned by the LLC seems unlikely how it is treated. That would get real complicated real fast if multiple assets are owned by the LLC.
If my 100k spent on shares is treated as a lost investment asset (when the partnership dissolves from a tax perspective), then my partner got a 100k cap gain selling his shares and I got a 100k cap loss. Makes sense, but doesn't feel like it is right.
If my 100k spent on shares is treated as an investment that has not been disposed, because I still do have the shares, then we just structured a way to spend 200k on a depreciable asset and dissappear 100k of that basis. Does basis really just dissappear like that?
So how does this actually play out? If it naturally plays out badly, how can it be done so as to avoid a bad outcome?