This is less of an issue here that what you all are describing.  

No business motive. 

Whether that is staying in the family business or doing something else.

Of these professional wholesalers, nearly all of them will be well capitalized professional real estate investors or large businesses doing hundreds of deals annually with many years in and around every part of the real estate investment journey.

I get where you're coming from, through the eyes of your CPA who has to process and file all of the tax forms and keep track of the basis in the Roth IRA it is less work and red tape to just take it from a brokerage account but at the end of the day it's a viable strategy to use the Roth the way you're describing.

Until I am considering building cash flow with launch an ATM business then using that cash flow to invest into BRRRR deals and then BTR deals. 

Tenants have dog allergies and chronic asthma; the persistent smell and the dog hair found in multiple areas so far are harmful to our health and have, can, and will exacerbate health conditions of tenants.We believe the issues described above present a materially dangerous or hazardous condition to the health and safety of our household.

LLC Taxation for FlippingSince you’re flipping the property in under 12 months, the IRS usually treats it as ordinary income because it’s considered a business activity, not a long-term investment.

This arrange that you will have will likely be a headache(major assumption on my part).First - Do not do business with a friend. 

Personally, I think this company is probaby about to go out of business - they have lots of inventory, and it's not exactly prudent to be investing in FL in the coastal areas now anyway.