He has been doing flips for 30 years and claims to pay a great ROI and get equity in the flip as well.

However, the seller claims he purchased the property as a two-unit dwelling based on Baltimore City public records, yet it’s not legally permitted as such.

Well, they claim that their leads are better because the leads find them:The only way sellers find you is when you rank #1 or #2 in that market. the lower you rank, the less leads find you. 

Any company insuring your properties without an inspection most likely has a clause buried deep in their policy allowing them to deny claims for conditions found on the property that do not meet their UW standards and they will deny you claim based on "the house should have not been insured with them anyway".Although the inspections can be annoying look at it from the other side.You pay them 1000 to 3000 a year to insure a rental property where they agree to pay out possibly hundreds of thousands of dollars if it burns down or up to 1 million if a tenant slips on a bananna peel and falls down the steps or the tenants dog bites someone and since you didn't enforce the tenant having their own renters policy to cover the dog bite the landlord's policy is paying out.The insurance company is very much like your rich uncle backing your business venture - you run the business, he takes on the financial risk from disasters, and doesn't even get a say in who lives in the property.Your rich uncle asking you to fix the steps, put up a handrail, etc which is in your and his best interest long term.Do you really want to rent out a property with a busted front step and a bad roof that is going to leak sooner than later?

When you make unfounded claims about fraud, incels, or Ponzi schemes, it reflects more on your lack of understanding than on the integrity of the Gator Method or its community.

Some of the hiring systems will allow you to see screenshots of when the VA claims to be working so you know they aren't cooking their timesheet as well.

If this is an insurance claim the process is very different than hiring a roofer during normal circumstances.  

However, I think the only 'handout' I think we need right now is the child tax credit which both parties claim to support.

I doubt Sherpa's claim!! 

Because the Adjuster's fee is normally a % of your claim payment, you may want to get estimates of the rebuilding costs and see how close the proposed settlement is before you decide if the Adjuster is worthwhile.