I know, I'm working with Norada right now on a property, and their founder Marco Santarelli is a frequent visitor to the BP forums.

You also may be able to find a suitable rent-to-own option.  

I understand, for long term BnH property, the best option is to replace the pipe.Any suggestions on what type (materials) of pipes are suitable for cold weather, like Chicago?

You can do this in parallel with step 2, but complete 2 & 3 before proceeding to 4.4) Identify the types of properties and areas that are suitable for your strategy and start intimately familiarizing yourself with that market.

It has some interesting features in that in the past it appears to have been owned by a contractor - it has a four-wide driveway suitable for many large vehicles - 200 amp service - two outbuildings (including a large workshop with windows and a loft) - a large add-on family room to the original house - and a wrap around back porch - a large single bathroom with a jetted tub and a tile patio area at the side of the house.  

A surveyor is for easements and lot lines.What you need is an engineer -- someone to tell you about the grade and suitability of building.

Pros: Visitors spend more time out in the evenings than a regular roommate.

And for that matter, if your plans progress, it might be worth taking a bit of a road trip and specifically staying in some tiny home rentals to gain a better understanding of the visitor experience.On a side note, I'm curious what type of insurance policy you'd need/be able to find for your intended use of the tiny home.

My realtor let me know that a traditional FHA loan may not be an option, and perhaps a 203k loan would be more suitable.

Bonus question: any tips for choosing a suitable title company?