Including the inconvenience this causes his tenants because now they just added another expense having to pay for a P.O.

Any additional expenses incurred in preparing the land for sale (such as adding driveways) would also be included in the cost basis.In summary, you would typically report the capital gain from the sale of each parcel in the year the sale occurred, based on the cost basis allocated to each parcel.

I came across this article about the recent Salt Lake City Council budget amendment that includes money for the city to monitor STRs via some type of software.

Be prepared to show stable employment and income history.Developing an Investment Plan:Market Research: Understand the local real estate market, including rental demand, average rents, and property values.

Would it be better to create an incorporation for management?

It's a difficult situation all the way around although sometimes the choices we make create our difficult situation.

This means that the Spanish government's rental price index will force us to achieve a paltry 2.5% gross return on our premium area apartment.Additionally, the situation with "squatters" (Okupas)  is worsening in all areas of Spain, including in areas considered "ultra premium" such as "La Finca" in Pozuelo de Alarcón, where footballers and singers reside (Cristiano Ronaldo lived there when he played for Real Madrid).

You can however as a cash buyer purchase a home near Indianapolis and some of the suburbs of Chicago (which includes Indiana) for $100K and rent them out between $1500 to $2500 per month. 

They have the experience and expertise to build a robust online store, optimize its conversion rate and handle the technical issues involved in creating a successful eCommerce platform.

You will be closer to $90,000 if you do this the right way and I'm not talking about the ADU being included.