This is a Rollover not a contribution so no annual limits on amount to rollover.

When you say "I am pulling funds from an IRA" do you mean you are taking distribution from an IRA and want to use those funds to buy investment property in your name or do you wish to rollover your IRA into self-directed IRA and buy the property inside of your SD IRA?

I didn't realize that the total amount I bid would pay the delinquent taxes in the current auction, THEN rollover to all the delinquent taxes for the following years. 

We live about an hour or so from our target market and want to pursue a BRRRR for the potential ability to continually roll over our funds and to gain more doors.

Does that roll over as a credit for future income or do the IRS actually send you a check?  

I have a TSP still in place which I would like to rollover to a SDIRA(possibly with checkbook control). 

Kind of like doing a rollover except with property.

Hello:As I proceed down my learning path, and as I continue to analyze deals, make offers, get rejected, feel sadness.....lather-rinse-repeat....I was intrigued by SDIRA's.I have a rollover IRA with enough money in it to fund several purchases (25% down payments anyway).

My question is: can I rollover the losses to this year if I sell regardless of income ? 

It's a great way to roll over your gains into a new property and potentially increase your returns.Lower Tax on Rent Income: Good news for real estate investors!