I am not sure what kind of company you are trying to set up, but if you are setting up an employing brokerage, at least in CO, you would not have any trouble finding coverage- CRES covers some, if not all, types of commercial transactions.

I ask for current & prior addresses, current employer, and take home pay. 

The best way to size up a company is to visit the office and meet the staff.  

This is self employment income.

To further my goals, i've built a good sized fund and am currently pursuing my real estate license.

Even if you write checks to Contractors, you can still make more return on investment than an IRA or other "boring" and  "safe"  retirement accounts.Many people are happy to have their employer match their retirement funds and then wait decades for the money to grow enough to retire or go on an extended Vacation.One of my longer term goals is to be able to take a 3-4 month long Vacation.I do ask what some of my non REI friends long term goals are and most just say to retire by 67.    

I work primarily on the south side of the city, but we can do work throughout the city and also the northwest Indiana area, (travel will depend on the size of the job).

It's not a one-size-fits-all situation.  

I would think 5k or 10k would be plenty, though it will depend on house size, age of roof, windows, sewer, AC, Furnace, electrical, plumbing. 

We just took off the old sheet material and underlayment and even after more than 15 years there was only one area about 1 foot square in size that had some wood rotting.