About the most practical option is Quigley or buying a 4 wheel drive chasis and putting a utility back end on it.In the winter, I really do need 4 wheel drive (one of my rentals is in Eastern Colorado - I regularly pass rollover accidents on a notoriously icy stretch). 

B) Capital gains hit on your taxes if you sell.C) Sell using the 1031 roll over, (to avoid the capital gains tax) but there are strict timelines you must follow in identifying a property and then on closing.

Sean, You can always try a rollover method (1031 exchange) and defer those taxes to the next one. 

The loan will be financed through a self-directed IRA and all payments will be paid into a Rollover IRA I have established.

Having a property roll over to another years costs money in taxes, insurance and DOM - days on the market is not a good selling point.

.• Contribution of 17k, left to double over said 15 years (low contributions years 1-5, then 17k year 6)• Goal of 1x rollover to Roth IRA of $35kSeeing conflicting information around that Roth IRA conversion.

Would it be best to roll over everything into a retirement account to avoid the tax hit? 

If this is a month where you don't do anything but put gas in your car, it will roll over to the next month, and you will be able to absorb an unexpected $400 expense.

Most will roll over to month-to-month.

If you decide to rollover your funds into a self-directed IRA, some things to look out for would be custodial fees (every custodian has a different fee structure), funding turn-around time, online account access, customer service (HUGE when investment deadlines are coming up), and knowledge and expertise over self-directed investments and IRS rules (this is extremely helpful when you are new to self-directing, you want to make sure you work with a custodian who can help answer these types of questions for you).