Properties are expensive so you need to really sharpen your analysis skills to make sure you are buying good deals.

Again, value add is solid IF you have a networth, or have specialized skill (mobile homes, storage, multfamily)Infinite returns with single family houses is the best way for quickly growing your networth, increasing cash flow and having velocity of money.

I've scheduled some time to talk to all of them to get a better sense of how their skill set aligns with my interests.

Along those lines, the skills/temperament required to effectively manage small properties is very different than the skills/temperament required for effectively managing large properties.

I currently work in software and would love to leverage some of my automation skills to streamline repetitive tasks related to real estate investing (if there are any!). 

It's a great place to sharpen your skills in that area. 

I do not have much of value to offer in regards to real estate, but am very skilled and knowledgeable in other areas.

You are bringing in the cash and he is theoretically bringing in some level of project management skill.

He has money and funding and would be doing/overseeing the work either way.If his skills as a contractor and my real estate skills offset each other, does it make sense to contribute the same amount financially? 

I would also like to learn skills to have other properties