@Rupert GrantGenerally if you're eligible for a Solo 401k, it makes sense compared to a self-directed IRA for many reasons: Compared to an IRA, Solo 401k contributions limits are roughly ten times higher.There is no custodial requirement for the 401k.You don't need the additional expense and administration of an LLC to have checkbook control.You can borrow up to $50k from the plan; IRAs do not allow participant loansThere is a built in-Roth component whereas IRAs are either traditional or Roth, not both.A spouse can also participate in the same Solo 401k plan.The Solo 401k has additional tax benefits over an IRA when investing into real estate using leverage.The penalties for prohibited transactions are less severe, though it's best not to utilize this benefit :)The one exception I can think of is if your primary goal is to self-directed Roth IRA funds.

This was a deal between family therefore, it was concerned an "arm's length" transaction in which we did not use a real estate agent.

(many of those guys end up being sued btw)Smarter way to transact business in a similar capacity to what you probably like about wholesaling would be getting a real estate license & selling properties that way.

The hardest part is spending 12 hours searching for a BRRRR and brokering the transaction on a 40-50k house and making peanuts.

The LLC recently bought it's first property, you did not... so that transaction would likely not affect your individual status as a potential first time home-buyer. 

We are using a well known broker for the transaction but we just haven't heard any stellar ideas for the other building.

No data entry except for 10 minutes at the end of the year to categorize transactions for my CPA.

Its been a slow go seeing the realtor is on both sides of this transaction and clearly wants the closing to happen on schedule. 

Also keep in mind this is the slow time of year for real estate transactions.

They do not operate separately and do not act separately because funds cross back and forth constantly and continually with no formal arrangement.