It was unfortunate we waited until early December to make the roll over (she transferred to a Roth once it was rolled over to the new SD custodian).

It might be best if you roll over to a BDRA or SDRA which allows you to transact directly through the account without any personal risk, this will safeguard your investment and you as well...

In principle, a 401(k) could allow in-service distributions that could be used to rollover funds from your employer-plan to a Self-directed IRA or Solo(k).

You have to roll over the value of your relinquished property (which you obviously intend to do) but you can add additional equity or debt as you see fit.

What you can do is a rollover (https://www.irs.gov/retirement-plans/plan-participant-employee/rollovers-of-retirement-plan-and-ira-distributions) from your employer's retirement account into another retirement account, including a self-directed one.

The Self-Directed IRA and Solo 401k Similarities Both were created by congress for individuals to save for retirement;Both may be invested in alternative investments such as real estate, precious metals tax liens, promissory notes, private company shares, and stocks and mutual funds, to name a few;Both allow for Roth contributions;Both are subject to prohibited transaction rules;Both are subject to federal taxes at time of distribution;Both allow for checkbook control for placing alternative investments;Both may be invested in annuities;Both are protected from bankruptcy creditors;Both are prohibited from investing in assets listed under I.R.C. 408(m); andNeither may be directly invested in your own business startup  The Self-Directed IRA and Solo 401k DifferencesIn order to open a solo 401k, self-employment, whether on a part-time or full-time basis, is required;To open a self-directed IRA, self-employment income is not required;In order to gain IRA checkbook control over the self-directed IRA funds, a limited liability company (self-directed IRA LLC) must be utilized;The solo 401k allows for checkbook control outside the LLC;The solo 401k allows for personal loan known as a solo 401k plan.If you borrow from your own IRA, it will be deemed a taxable distribution;Unlike an IRA, a Solo 401k can invest in life insurance;The solo 401k allow for high contribution amounts (for 2015; the solo 401k contribution limit is $53,000, whereas the self-directed IRA contribution limit is $5,500);The solo 401k business owner can serve as trustee of his or her solo 401k;The self-directed IRA participant/owner may not serve as trustee or custodian of his or her IRA; instead, a trust company or bank institution is required;Unlike an IRA, generally when distributions commence from the solo 401k a mandatory 20% of federal taxes must be withheld from each distribution and submitted electronically to the IRS by the 15th of the month following the date of each distribution;Rollovers and/or transfers from IRAs or qualified plans (e.g., former employer 401k) to a solo 401k are not reported on Form 5498, but rather on Form 5500-EZ, but only if the air market value of the solo 401k exceeds $250K as of the end of the plan year (generally 12/31);When funds are rolled over or transferred from an IRA or 401k to a self-directed IRA, the amount deposited into the self-directed IRA is reported on Form 5498 by the receiving self-directed IRA custodian, generally by May of the year following the rollover/transfer.Rollovers (provided the 60 day rollover window is satisfied) from an IRA to a Solo 401k or self-directed IRA are reported on lines 15a and 15b of Form 1040;Pre-tax IRA contributions on reported on line 32 of Form 1040;Pre-tax solo 401k contributions are reported on line 28 of Form 1040;Roth solo 401k funds are subject to RMDs;A Roth 401k may be transferred to a Roth IRA--from a planning perspective, it may be advantageous to transfer Roth Solo 401k funds to a Roth IRA before turning age 70 ½ in order to escape the Roth 401k RMD requirement;Roth IRA funds are not subject to requirement minimum distributions (RMDs);The fair market value (FMV) of assets held in a self-directed IRA is reported on form 5498;The fair market value of assets held in a solo 401k are reported on Form 5500-EZ;At termination, the solo 401k is required to file a final Form 5500-EZ and 1099-R; andAt termination, the self-directed IRA is only required to file a form 1099-R.

I have a friend that wants to lend on some deals, but he needs to rollover to an SDIRA that gives checkbook control.Do you know of a provider that I can recommend?  

I need to live in condo until Nov 15 for the 2 out of 5 gain rollover or rent it out and then live in it for 2 months before I sell it.

Among 401k's that are not self-directed, either the old plan or the new plan may likely disallow the rollover.

Another option is you could let it roll over to month-to-month lease, which would keep your property rented, but give you more flexibility to not renew if the late pays continue.