I’m a new investor based in Chicago, but willing to relocate to nearly any city in the Midwest.

It's a plus if they offer any good bundling options for an umbrella policy for 2-3 homes, as we're looking to get one for the first time.I know some insurers have been leaving the CA market recently so looking for updated recommendations based on your personal experiences.Thanks!

My biggest concern is the flood certificate says the main floor of the property is 3.7 feet above Base Flood Elevation.

Will you want or need to rezone based on what you wish to build?

I'm hoping one day this will make a good story, but if there's any other words of advice, I'm open to it all.

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.

I say you should weigh those options for yourself based on research.

The life estate will spell out the obligations of the step-father (taxes, utilities, insurance, upkeep - or even a base rent that you could use to cover those costs).

Set a goal, work backwards, and create a realistic strategy based on your personal abilities.An aggressive investment strategy can get you free from your 9-5 in about 3-5 years.

Based on comps and recent sales I know the property is worth 120-140ish.