We are creating an LLC taxed as S corp:  Oakbrook Property Management to manage our taxable rentals ourself.  

When that property is sold, the IRA's capital is being reallocated from holding real property to holding cash, and this is not a taxable event.Keep in mind, with an IRA, YOU do not receive the profit on a short term or mid-term basis.  

ACV is cheaper but again you will get a depreciated value if you make a claim.... also make sure you have medical coverage on the policies, and try to purchase the PUP from the same carrier that is insuring the structure. 

S-Corps also have the added benefits of non-taxable dividend distributions, which is not the case for C-Corps. 

Am I getting something less with the cheaper companies?

If you do pull any funds out - it would be considered a distribution, which is a taxable event and if this happens before retirement age penalties would also apply.In addition that that, flipping activity may be considered an active business, and profit might be subject to Unrelated Business Income Tax. 

Rent is cheaper 65% then section 8 program (smaller payout)I prefer to put the property on section 8 because i KNOW that i will receive my money, or at least most of it.

It is much cheaper and I would certainly prefer to pay my friends and family before a HML. 

An individual generally must include any pretax assets that are converted to Roth IRAs in taxable income, but the 10 percent early distribution penalty tax does not apply.Any basis in the Traditional IRA (e.g., nondeductible IRA contributions, retirement plan rollovers of after-tax assets) is not taxable when converted.Tax laws require individuals to treat all of their Traditional and SIMPLE IRAs as one IRA when figuring the taxation of their conversions.

sounds like you should lower the rent. depending on what you're asking, i'd drop it 8-10%.... still cheaper than a month's vacancy.