I have capital and would love to learn more about gap lending, helping flippers and wholesalers, but i need help learning how to best structure those deals, make sure title companies account for it correctly, etc. 

Hey Milind, I'm a local broker, investor, and property manager (100+ STR/Airbnb properties in addition to LTR).We offer mortgages through our subsidiary company, wholesale to over 100 banks and institutions.

There's companies that fix everything. 

To answer your question, I would say you need +100 keys to achieve the economies of scale and feasibility to hire a property management company.  

Couple ways to size an umbrella policy, 1 is to analyze your assets and do it based off that, but I have always preferred to do it based on what is an amount that guarantees my insurance company would want to defend me. 1 million to start is pretty popular.

You should search on Meetup.com, Eventbrite, Facebook, and the Bigger Pockets Marketplace. 

These platforms pool funds from multiple investors to invest in a diversified portfolio of real estate projects.Real Estate Investment Trusts (REITs):REITs are companies that own, operate, or finance income-producing real estate across various sectors.

To answer your question, I am not familiar with that DIY company but know of another one that a peer uses that might be lower for a property of your type.  

Company is Wholesaling PPC, we might be a good fit for you.

For example a lot of property management companies want the owner to indemnify the property manager even if they were at fault / potential did something illegal.