Those habits roll over into becoming good with managing property and being a landlord

ROBS stands for Rollovers for Business Start-ups.

Also having been born in England I grew up with my dad wanting me to play football, I feel like he would roll over in his grave if I didn't take the chance to meet a pro football player.

Its called ROBS - Rollover Business Strategy. 

Beyond investment savings I have 401K and Trad IRA (rollover). 

There is no ‘middle man’.As the trustee of the plan you go to any financial institution of your choice (a bank, credit union, brokerage firm such as Schwab of Fidelity) and open non-custodial account for a trust.You request a direct rollover from your Traditional IRA or former employer 401k and in few days receive a check payable to (for example) ABC Solo 401k Plan FBO John Doe.You deposit this check into newly established bank account for the Solo 401k Trust.Now that your plan is funded you can make investments as simple as writing a check.

Having said that, you should keep your existing Traditional IRA and Roth IRA at your current custodian, do the backdoor Roth there, then simply rollover Roth funds to SD Roth IRA.

To qualify for Solo 401K you need “earned” self-employment income.If you were eligible - you could rollover any retirement plan into Solo 401K except Roth IRA (IRS does not allow that).

I am not in favor of that, I don't just roll over, just because someone is pushing. 

All I know is there is a once per 12 months rule for in-direct rollover.