You can either continue the depreciation schedule from the property sold, and create a new fixed asset for the additional amount invested to obtain the property (Two Depreciation method), or you can opt to treat the new asset as one asset (Single Depreciation Method).

Almost all my communication is through texts.

I did look at some of the material participation criteria and we should easily surpass the requirements since we pretty much spent time improving the home ourselves, managed all guest communication, etc.Thoughts?

Full stop.Unique style, ample amenities, good location, great photos, solid communication, etc etc. 

We self manage.We've hesitated to list anywhere else mainly because we communicate with guests exclusively through AirBnB.

None of these changes were communicated until right before closing.

The reason why that approach is effective is that those communication channels will be less saturated with competition, and also attract more actively interested people.

The agent has been communicative the whole time (something that I can say about 5% of agents in my limited experience) so I'm a fan!

I'm not familiar with Wisconsin laws but selling or assigning a contract is only one method of wholesaling. 

\I will say, as a PM, where I add the most value if the 24/7 guest communications, 20+ platforms including some big names like JetBlue and Marriott, pricing with RevMax and a live revenue manager, etc.