We haven't stayed as guests for 2 years.

This a was a deteriorated house on my street that was previously occupied by a drug dealer.

They are known as the Winthrop Factors-The purpose for which the property was initially acquiredThe purpose for which the property was subsequently heldThe extent of improvements made to the propertyThe number and frequency of sales over timeThe extent to which the property has been disposed ofThe nature of the taxpayer’s business, including other activities and assetsThe amount of advertising/promotion, either directly or through a third partyThe listing of the property for sale through a brokerThe purpose of the held property at time of sale; the classification as an investor or dealer is determined on a property-by-property basis.To me intentionally buying a property to renovate it to resell it for profit, twice in the same year, and opened an entity to do it in ....is going to be ordinary income and not capital gains. 

I opened an  partnership LLC, and I am learning now about taxation it will be treated as a dealer and not as an investment.

Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

It is in an enclosed gate area that can only be opened from inside the fence so I'm leaning away from using it as storage space while I have other guests staying there.

Having Dealer status subjects the income to SE tax; but even then it doesn't apply to the real estate dealer's rental income.

This company is a complete real estate and investment ponzi scheme.  Run by Dutch Mendenhall and Amy Vaughn, they solicit hard money loans (which they do not pay back) and joint venture real estate deals which they al...

It isn't a big job but I don't want things to go south so I stay in it.Of course I practically live on this forum so I pass along any pertinent info I find as well as answer questions.

Set a new price record for the street and got rid of the drug dealers Lessons learned?