If not I will see if I can find one to chime in.There could be other specific circumstances that cause a taxable event, but in general this is the strategy and I have seen it work well.  

With the Duplex now, my understanding is I file as though the rental half is a separate property and cut all expenses in half as a write off to my rental income (property tax, insurance, maintenance, improvements, etc...nothing was done specifically to either unit it was full home external work like garage and railing repairs, painting) as well as depreciating the half of the duplex that is a rental after calculating basis.It all seems very straightforward to me but I know I'd be naive not to have a second set of eyes with a professional given my lack of experience.

Hi Jane,I would not say that the decision to create an entity or not comes down to the number of properties that you own specifically but will more likely be based on your risk aversion.

I think the suit would be for specific performance not to overturn the sale. 

At this point, I'm not usually recommending that folks new to the STR game start more units if they are specifically looking for a passive investment.

Are you looking in a specific area? 

Maintaining detailed records of mileage, receipts, and other relevant documentation is crucial, and your CPA can provide specific guidance on this.

I'm not a tax pro here, but I don't think 1099 vs W2 makes any difference other than the specific reps requirements.

I am curious what tax benefits I can claim, if any, specifically:1. 

However, an essential exception emerged in the 1990s, allowing specific rental income to be categorized as non-passive.