It actually helps  a lot in terms of capital gain tax as well.

Determination of whether an individual is a real estate dealer is related to SE tax.Rental activities are not subject to SE tax unless the following situation applies.Income from rental of real estate is excluded from the definition of net earnings from self-employment and is therefore not subject to SE tax[Reg. 1.1402(a)-4] Exception: An individual who is a real estate dealer is subject to SE tax. A

Any attempt to form an LLC and manage the transfers like that will probably result in the IRS claiming you are using a "step transaction" - a series of legal steps by themselves used to avoid compliance with IRS law in an attempt to avoid tax.  A

@Ann Wing make sure to understand the HOA as others have said but also the Special Use Tax as some areas around Denver have some sneaky hidden fees that may seem minor but add up.

It is certainly not the kind of savings that induces once to "create" self-employment just to avoid that tax as is so often recommended here on BP.

In Washington, renting rooms can be called a boarding house and as such requires collecting sales tax, a license and many more hassles.

Income from flipping is ordinary income and subject to state and federal income tax as well as self employement taxes (i.e., both halves of medicare and social security.)

A well crafted option to purchase as opposed to a rent to own contract would also allow you to lease the property for 1-1.5 years as you said and then 1031 exchange into a new property deferring the tax.  A

I had good experience with turbo tax a W2 and multiple rentals for years.  

The point that you are missing is that you are not "just" responsible for the income tax, but for the payroll tax as well.