Consider offloading an underperformer, or a high equity property and getting better, larger or more assets.

I get FinTech is a high-risk activity, but imagine the industry will consolidate to one or a few strong players.

This is a beautiful house - rehabbed/looking new and fresh - walking distance to the water etc, yet low gross yield  compared to Byrd (???)

I highly recommend finding a broker and have them find a policy that meets your specific requirements.

.- I would highly suggest you plan on using a property management company.

While this is a great and highly motivating goal, most people are either clueless or incorrect in their belief as to what is required to obtain this “lifestyle”.Understanding of the “how to” get there is further obscured by the misleading, and often patently false “pathways” sold by real estate educational MARKETING companies as workshops, upsold to association memberships, upsold to mentorships.

Is my thinking correct that homes in highly appreciated areas won't benefit as much from Cost Seg. 

Utilities are OFTEN overlooked so reach out to power, telecom, gas (or go all electric), water, and sewer to make sure you understand what it would take to get separately metered services from the primary house.

I know a lot of Chicago investors are here too; but if you were in my spot would you recommend Chicago as prices are too high and I have never been to the city moving next year.

@Nathan Gesner you just have a high value lesson to everyone.