this is getting to be a rather entertaining thread :)

As someone who lives in hotels 365 days/year, let us not forget theatrical/entertainment tours (certainly a very small percentage, but we do nonetheless). 

You could pay all this debt off in a year, if you were to work two jobs, sooner if you can sell some of the stuff you bought, unless it all went to consumables, like drinking and dining out and vacations and entertainment.  

The second house in the back had someone back into the front and did damage to the kitchen wall and the seller is entertaining cash offers only.

Now we've started investing out-of-state, so we're entertaining the idea of selling the townhomes and using the proceeds to acquire more units elsewhere.

Our main idea around choosing Lake Tahoe is the year around entertainment attraction.

Marxism would not entertain those things to begin with in the first place.

I ask this question because there are real differences in what you are allowed to deduct, capitalize and report in these two situations.Investors that are wholesaling and flipping are typically in the business of real estate.Landlords typically are not in a "trade or business" as defined in the IRS code & regulations, but are engaged in an investment activity (Production of income).Deductions that are reasonable and necessary in the production of rental income are not necessarily the same as what would be considered reasonable and necessary for a business.A business would be allowed research and development costs, educational Seminars, trade shows, meals and entertainment.

Yeah, you make your money when you buy.One good thing about "the deal," is that it can be a retirement activity that finances our later years, while being highly entertaining.

If the deal is damn good then I would entertain this otherwise more disadvantages than advantages to taking out of your 401k.