This made me rethink some things and I’ve spent all day taking action on this persons initial analysis.

I do think the contractor who came in person seems like a trustworthy guy but it’s the first time I met him.Lastly, should I be the one to provide a contractor agreement for them to sign before getting this work done?

That seems a gross oversimplification that can result in bad returns.I've personally invested in some low cost markets that gave me great cash flow and above average appreciation.

Things are tight with day care, mortgage for personal home, and kid #2 on the way.

@James Kim hi James, yes I have actually been in an apartment building where my personal rent went down slightly.

Condo HOAs can have personalities to manage but can keep the property in better condition and can cover some expenses. 

Spouse, father, biotechnology engineer (by degree), water engineer (by experience), specializes in natural health, loves the world of personal development, and the world of real estate.- what am I doing here?

. 🕵🏽‍♂️ And if you have a willing buyer but that person is buying it as a second home or as an investment, no $10k for you!

For owners it would be that they think of you as their own personal assistant and not as a professional and they monday morning quarterback every little thing that goes on in your property. 

Others might be fine with taking risk, but least by doing this a person can get an idea of what might go wrong.e) Legal document analysis: it will usually take a few days to go through the legal document properly, as almost inevitably there are tons of gotchas that either have to be explained, or mitigated with a side letter.That is the very short summary of what I do.