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

I wouldn't recommend doing cold calls for someone, but if they have an off-market system you may offer your skills to help them get appointments for ones on the fence.

Being able to understand and readily provide the building department with what they need is a skill that architects and designers must develop.

I am very handy and skilled and also well networked..

Guess Ill learn a new skill

Owner is an interesting old guy with cool stories & skills, so it was great to walk his property with him. 

So to answer your question a bit more succinctly, Zillow is great for easy comps in fairly uniform neighborhoods but when it's a bit less simple I like to consult others who are more skilled/experienced than myself.  

I was thinking about trying to become a part time real estate appraiser to help me with these skills. 

Tricky part to that is that you have to cut in with a brush and roll at the same time otherwise the edges will be really noticeable, so you kind of need 2 people working together, and you have to roll almost to the very edge of where you cut in, but you don't need any special skills other than knowing how to roll a paint roller on the wall.