I currently have one SFR rental property in Indianapolis and looking to expand into multi-family, mainly for the purpose of more cash flow.

You need to adhere to the terms of the current lease if there is one. 

Purchase price: $100,000 Sale price: $112,000 One more wholesale deal in the books.

I'm a travel RN with a few flips under my belt, one commercial property that turned out well, and am looking to purchase a property in New Braunfels, Tx to live in for potentially 6 months out of the year.

I may be a little bit biased, but I believe Chicago is one of the best cities in the country to house hack.   

One downside is the increased cost of insurance.

I'm trying to verify if this is correct and if so, how much more expensive (ballpark) can the one without standard exceptions be?  

That should take the most time - determining a realistic ARV and market rent should be the work of just a day or two.If the numbers all work and you've satisfied yourself with the neighborhood, it's time to put one foot in front of the other by making an offer.

In my market the jump from a 2 to 3 is a big one, 3 to 4 not so much.

Although I believe I can see the path to my first rental easily, I'm having a hard time figuring out how I'd get to the next one.