Are there better companies to buy these homes from?

Here are some tips to get you started:If you don't already have one, request a copy of your community's governing documents from your HOA board or management company.

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. 

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.

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.  

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.  

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.