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Approaching the pax is legal, but exceeds the TOS in the same way that carrying a defense weapon is legal but exceeds the TOS.
Absolutely ask your insurance agent if claims will be honored if driving for hire off app!
Many insurance companies will even deny claims if you are on app but don’t have the rideshare waiver, and yes - they check and U/L will rat you out.
Also your insurance can drop you and if they’re in a bad mood can call a submitted claim insurance fraud.
If your insurance company says it is ok then go for it.
In most if not all states you don’t need a commercial license or DOT number or commercial plates if you are not carrying more than 8 pax or having a vehicle weight over 10,000 lbs.

The way Minnesota laws are written is scary. By strict definition Door Dash drivers need both a commercial license and a DOT number. I have never heard of this being enforced. IANAL and IANALEO though I have played one on Halloween.

Commercial Motor Carrier Requirements

If you operate any class of vehicle as an employer or employee, you may be subject to commercial motor carrier requirements. This includes driving single unit and combination vehicles of over 10,000 pounds GVW (such as construction vehicles), and vehicles used to deliver packages and other articles. Also included are vehicles designed or used to transport more than eight passengers (including the driver) for compensation. The requirements may include the need to possess a valid U.S. Department of Transportation (DOT) medical examiner's certificate, and restrictions on the number of hours you may drive. There may also be vehicle maintenance, insurance, and inspection requirements.
 
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