I'm an investor and a licensed mortgage broker so I'd be happy to talk through my experience as both.

Totally agree with you and it looks like I need to get a business license to do the intermediate leasing occupancy (ILO) in SF.

Our systems have caught people using SSNs from deceased people or the SSN indicates they are 2-3 decades older than their driver license birth date.

I notice you didn't say you'd actually seen the tenant's policy.Are they properly licensed?

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

Here is a good video The Ohio Division of Real Estate made about wholesaling in Ohio https://www.com.ohio.gov/real/ I recommend you just get your real estate sales license.

This contractor has 0 reviews on yelp which I found a bit sketchy, but was able to vet him by his contractor's license, worker's comp, and by visiting some of his ongoing projects.

I pitched her even getting a real estate agent license to contribute to the venture as she used to sell new construction when she first started out in sales.Ultimately, you are asking them to put a huge amount of trust in you and go along with making a large financial commitment with you.

We hold a license and face criminal penalties . 

I have several quotes in the $20k-$30k range - before finding a 'mom and pop' licensed electrician who did it for $9k.