Hard to say without all the numbers, but I will say this not an unusual set up for the area....and also we have very few duplexes here in Jax, so if the numbers work I am not seeing an issue with the ADU.

Do I put the address for both of these on the contract as the address or just the house and land parcel?

Like I do for my practice, she works with clients remotely, so distance is not an issue.

There were some issues during inspection we were able to use in negotiations.

It will go on your schedule C just like any other rental income. so no issues there as you would not even need to show leases. 

However, in the short term here are the issues I see:Some buyers will try to save money by going to the listing agent.  

The only crime issues I have had are when a property is vacant. 

I met with someone I am interviewing for a job that also owns real estate and he began a preliminary very cursory review of my portfolio and immediately stated that given the current market value of my portfolio and the number of “doors” that I had my CoC return really needed to be addressed before I considered purchasing any new properties because it was too low and my current level of cash flow needed to be looked at because he also felt that should be higher.

But you can still treat it as resulting in Ordinary Income even though it is reported on Schedule E, which lets you properly report in accordance with the tax results it seems you are shooting for under the tax return loophole.If your CPA is looking at switching it between schedules to get that tax result...it sounds like they don't understand the reporting position fully and/or they just don't know how to use their own software to address it.In summary, based on what you are describing for the situation, it should go on Schedule E, with what sounds like the resulting refund of $17k.

@Amelia Gull @Dave Foster can answer about any non arms length issues…he’s our expert.