Consult someone who actually knows what they are talking about/does this for a living, but most of your tax savings are only going to offset the earnings of the partnership rather than one of you individually.

In the first you have one tenant, 2500/mo revenue and higher costs.

Connecting with investors is a great move too; it’s one of the best ways to gain real-world knowledge and build a strong foundation for your journey.What kind of investing are you most interested in? 

What are the largest pitfalls one may run into that turn this from a 150 to 350 ordeal?

This group is an incredible collection of midterm rental hosts who support one another by offering advice and suggestions, being a sounding board for each other, offering mentorship and collaboration opportunities and share our respective networks.

Keeping clean records from day one really helps when tax season rolls around.

Some complaints I've gotten is that my unit only has one bedroom and is small square footage wise.

Or one that can be easily adapted?

Start by analyzing cash flow and market demand for each property to decide which one to rent out.

I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.