Also there are weather issues with Indiana winters and pipes possibly freezing, thunderstorms and hail damage2) Knowing how long to hold onto a property, 1031 exchange it to another property or DST, or in some cases sell it and pay the small capital gains tax (if any) to have less headache. 3) Underwriting the deal incorrectly (factors: local appreciation, rate of rental increase, economic growth, gentrification of area) and being overly optimistic (a renovated 100 year old home is still going to have problems).

I would refer back to your owner agreement and hold their feet to the fire. 

That being said, House Hacking is such a great way to start and choosing a multi-unit is something I would have done if I can go back in time.Good news: Illinois is NOT a community property state, so getting married won't hold you back (if you want to put the mortgage in either of your names individually).Easy way for you to calculate what you'll be qualified for: (Gross monthly income) x (57% max FHA DTI Ratio) - (Minimum monthly debt payments that show up on your credit report) = Max Mortgage Payment you can "afford".

After doing a few jobs with others who are investors, I’ve decided to dip my toes in the game and am looking for flips or light-mid rehab and holds. 

Usually, one party has more funds and the other party has the experience and time to be more hands on with the business. 

I was immediately put at ease with how they would take everything off of our hands.

Most people haven't done very many deals though, that's why they benefit from working with a professional.Some recent examples in my 1st hand experience... last year I witnessed a FSBO seller leave $400k on the table. 

I am based in NJ, but am targeting the South Bend, IN area for my first rental (primarily interested in long term rentals using the BRRR and buy-hold strategies).I am new to investing so I would love to connect with other investors, agents, lenders, property managers in the South Bend area or anyone who focuses on out-of-state investing as well! 

By forming a separate LLC to own and hold each legally titled separate property or business entity, theoretically only the assets owned by a specific LLC would be subject to claims or lawsuits arising against that LLC.

I don't know if there's anything I can do for you from here in Hyde Park, but I do have a little capacity in my day-to-day schedule, so if an offer of a pair of helping hands down this way would be welcomed, consider it offered!