On one hand, everyone has stretched further than the ordinary employee type and is seeking a better life.  

The IRS has an argument that the intent of the seller was not for speculation or investment purposes, rather, to deal the property in the ordinary course of business.

With wholesaling or fix and flipping any income is ordinary income and subject to state and local taxes at your marginal rate as well as self employment tax (i.e., both halves of social security and medicare.)

Flipping is a job (for most) and profits are taxed as ordinary income. 

If you are an ordinary income business we can only realize the HUGE tax benefits of the S-Corp election as of the date of incorporation moving forward.

That's taxed as ordinary income, up to a 25% maximum rate. 

Considering your gains in the IRA are taxed as ordinary income and your buy and hold are pretty much tax free, from my perspective you come out way ahead.

PROPERTY MAINTENANCE: Except for ordinary wear and tear and Casualty Loss, Seller shall maintain the Property, including, but not limited to, lawn, shrubbery, and pool, in the condition existing as of Effective Date (“AS IS Maintenance Requirement”).

Hey guys, I totally agree with following the neighborhood- we always do.I'm doing a major 4plex renovation condo-split in a growing part of town and thought about it since I'd be getting 4x the "benefit" while only having to panel one building.It would be out of the ordinary in that area, so I was curious if anyone has done comps on something like that.

@Jay Hinrichs  IRC Sec 162  "ordinary and necessary"Depending on OP's risk tolerance and sleep, it might make sense to take advantage of his (I presume) real estate professional tax status and invest in low to no cash flow, high appreciation real estate assets with leverage that will produce a material tax loss.Answer as always: it depends.