I have invested a large sum of money with a company (individual with LLC) who has filed chapter 11 bankruptcy.

I have used two management companies in Akron and both made me really appreicate self managing.

HOWEVER I just met someone from PadSplit, and partnering with a company that specializes in that could be a really great approach.

. - I believe that companies and the economy as a whole have begun a long-term shift towards back to in-office.

@Jordyn Gegg - I have a PM company that oversees all of my individual LLCs.

Assuming you no longer work at the company sponsoring your 401(k) you could look to move it into a self-directed account. 

it is hard to get on the radar of insurance companies. 

Say the wholesaler will profit $10k for assigning the contract to a buyer, and needs $2k EMD, then the gator will pay the EMD to the title company, and it is written in the contracts to the title company that the gator will get a profit of $1k, and their $2k will be returned to them. 

The company that I work for has a policy where the tenant can break the lease with 30 days notice before vacating the property, but they have to pay for an additional 2 months worth of rent.

We just moved across the country and our primary residence is now listed for rent through a property management company.