To my mind both of these would be prohibited transactions but I wanted to make sure I wasn't missing anything.Thank you

What is the scale of the transaction and how is the funding structured?

And then cross check that against the rent roll or whatever your estimates for the rent is.It might be some work, but digging into historical caps when the owner purchased might give you an idea what the markets done, or if the owner just made a really bad choice then paying $750k.Best of luck - sounds quite exciting with some potential!

@Shakaria Brooks my first wholesale transaction was a lengthy process.

I don't want to create an extra 20 hours of work for myself each week, as we have so many transactions happening.

Lurkers: Whenever you have a mortgage imminent or underway, you NEVER do any significant/unusual financial transactions without checking with your LO.

@Jacklyn P.No, your IRA can not lend money to you or the company you own, that would be considered prohibited transaction.

California LLC's are a nightmare administratively and cost $800/year to the state.If you work with good counsel, you should have no significant risk of prohibited transactions, and the risk is exactly the same whether you write the checks or have a 3rd party custodian do so on behalf of your IRA. 

I'm now looking into larger priced homes so that I can possibly cross collateralize, put more money down into another home. 

But separating the two transactions on the calendar.