2) this is an investor I plan on keeping for many deals, is there a way to create a fund that will allow me to not only roll over the capital he has invested but also pool the funds from multiple investors (Reg D maybe?). 

But trust me we are not taking a break to bask in anything - we are moving onto the next one and yes we are planning to refinance and rollover the funds toward the next project(s).

There is a brokerage account I can withdraw from, as well as an old employer 401(k) that I have been debating to see if I can roll over into a self-directed.  

My game plan was to rollover my 401k to a checkbook IRA LLC.

Escalating prices or creating additional holding periods, roll-over, additional option prices can disqualify an option and cause issues, so ensure an attorney familiar in options and financing is there.Options on lots have going to 3 years is common too, required to break ground after it is exercised, be aware of Dodd Frank financing options to homeowners by builder/developers, you're in a different boat.

@Troy Harbin Buttons:Vote: You like the post and click it, helps the BP member get noticed.Connect: You can connect in a couple of ways (roll over).

Complete a couple of those, and take the profits to roll over into buy and hold properties.  

Following are the similarities and differences between the solo 401k and the self-directed IRA.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 creditors;Both allow for nondeductible contributions;Both are prohibited from investing in assets listed under I.R.C. 408(m); andThe 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 (IRA LLC) must be utilized;The solo 401k allows for checkbook control from the onset;The solo 401k allows for personal loan known as a solo 401k loan;It is prohibited to borrow from your IRA;The Solo 401k may be invested in life insurance;The self-directed IRA may not be invested 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 the solo 401k;The self-directed IRA participant/owner may not serve as trustee or custodian of her IRA; instead, a trust company or bank institution is required;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 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 (Note that 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 RMD requirement applicable to Roth 401k contributions including Roth Solo 401k contributions and earnings.)

Checkbook control, higher contribution limits, no UBIT/UDFI tax on leveraged investments, ability to borrow from your balances for any reason, etc.Also, note that if you have Roth 401K balances, I believe you can do a rollover to either a Solo 401K or SD IRA, but you can't roll over Roth IRA balances to a Solo 401K for some silly reason.  

You can however establish a self-directed IRA and rollover your old employer 401k into it.