Limiting Tax liability as a flipping company

[Matthew T.]

I started another LLC in 2017 with a focus on wholesaling and flipping homes. We held nothing in this company and sold everything no longer than 5 months. Our CPA is saying we will be classified as a dealer/trader and subject self employment tax on the first 150k then regular short term capital gains tax. We did well over the 150k and are setting up to double or triple in 2018. My question is what do other large scale wholesalers and flippers do to minimize their tax liability? One of my partners is suggesting renting for 366 days then selling about 50% of our housing stock to save short term capital gains on most and then we would not be classified as dealer/traders. We do have a decent profolio of rentals already I just would hate to add more to the mix that are short-term. Then we would have to worry about more turnover and what if the market corrects? Hope to have a great discussion. Thanks Landlord Ninja

[Ashish Acharya]

@Matthew T. 

Sorry for the long reply, but looks like decent amount of money is at stake. 

• Yes, those houses you sold are inventories for you. So, the gain is an ordinary income(not the capital gain). Although the tax rate is same for the (STCG) Short-term capital gain and the ordinary income, the income from the flip sale cannot be classified as STCG because STCG has other benefits.
• You should elect to be taxed as S-crop. IDK when you started your LLC but there is a procedure that ou can retroactively elect to be S-corp. That way you will not pay SE taxes on your Net Income. You have to pay FICA tax on the salary you pay to yourself which should be less than 150k, I assume. Reasonable salary. You save a significant amount of tax this way.

Changing a deal status is not as easy. It is all based on fact and circumstances.Yes, classification of gain as capital or ordinary is determined property-by-property, so you can be both dealer and investor, but you will be a prime suspect for an audit.

The frequent buying and selling of real estate indicates the taxpayer is engaged in the trade or business of real estate sales. Taxpayers who can show that the time they devote to real estate activities is insubstantial compared to the time devoted to their normal occupation may be able to preserve capital gain treatment for the property they hold, despite some frequency in sales. Taxpayers who engage in more frequent real estate sales still may be able to prove that the sales represent an investment activity when compared to their primary occupation. This may be particularly true for professionals such as doctors, lawyers, and business executives. (This is not your case)

To determine if the taxpayer is a dealer generally three questions must be answered (per court cases):

(a) What is the taxpayer's trade or business? - Yours is not just rental, when you sell the rental house after 366days , IRS will look at if you were trying to funnel your dealer sale via rental activity to get Long term capital gain treatment

(b) Did the taxpayer hold the property primarily for sale in that business?

Determining if property is held primarily for sale to customers in the ordinary course of business is based on the facts and circumstances. Among the facts to consider are the-

• owner's original intent (nature and purpose for which the property is acquired);
  
  • Per court case, the taxpayer's primary holding purpose over the entire course of his ownership of the property [Not just time of the sale]. I am not saying that original intent can never be changed, but what you are trying to do clearly shows that you are holding property 366 days just to avoid taxes. IRS will come at you.
• extent of improvements and advertising to increase sales;
• number, frequency, and substantiality of sales [this generally is the most important factor See (c) below
• duration of ownership;
• continuity of activity related to sales over a period of time;
• extent and nature of the efforts to sell the property;
• extent of subdividing and development to increase sales;
• use of a business office for the sale of the property; and
• character and degree of supervision or control over representatives selling the property

(c) Were the sales ordinary in the course of that business?

Sales are ordinary if they are normal for business, which may be based on their frequency and substantiality. Per court case, Frequent and substantial sales of real property more likely indicate sales in the ordinary course of business, whereas infrequent sales for significant profits are more indicative of real property held as an investment.

In your case, it will be frequent because you are planning to sell even more. 

However, to get long-term capital gain treatment on the sale, if you have an actual investment property and you are a dealer too:

• Maintain separate book
• Document intent to hold the property as investment property in Minutes or other documents
• Report expense as investment expense on tax return
• Also, use separate entities.