I'd highly recommend house hacking in your local market since you're in one of the highest cost of living areas in the US, especially if you're renting currently and planning on staying in the area for 5-10 years.It sounds sexy to go out and invest out of state for your first property.

Question: assuming an ideal brrrr that has all investment extracted at the refinance, why would you choose a low cost market over a high cost market?

The risk of property damage or a lawsuit from a dog bite is too high. 

Start with durable, high-quality basics: plush towels, soft linens, and a fully stocked kitchen with sharp knives, pans, and essentials like oil and spices.

My known options are hard money or private lending and then maybe doing a cash out refi, but rates would be high on both ends and will really cut into my cash flow. 

The payments and interest are high.

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

I highly recommend working with him, but only if you're willing to put in the effort to build a business and though leadership brand!

Communication is highly important to me as well. 

I'd say the amount of time for the labor seems high.