At the moment I have about $30,000 that I could comfortably invest into something.

At that point, I felt comfortable moving forward on house hacking. 

If you feel comfortable drafting the deed yourself and going to the County Recorder to record, you may be able to do it that way, but be wary of unnecessarily screwing up the chain of title or marking something incorrectly, as often happens with DIY projects in the legal world.

He kept pressuring me saying if  he put in put of his own money to make me feel comfortable.

If you’re comfortable with these risks, it sounds like a strong path toward reaching your portfolio goals.

From your past posts, as well as what work you've mentioned being comfortable taking on yourself, I think you definitely have the requisite knowledge to act as your own GC and sub out any work you don't feel like taking on yourself. 

I have seen amazing stories from many of you on BP and want to open my mind to new possibilities and strategies that are out of my comfort zone.Teaching - I have been building residential and commercial properties for many (too many) years as well as land development and property subdividing.

I travel a lot to all my clients back east so I do get out to fine dining on those trips..

Get out of your comfort zone.

This gives much better diversification protection across geographies, asset types, strategies, investment subclasses etc. versus putting all the eggs into one basket.The downside is that it's not for everyone, and a person has to be comfortable with turning over control to someone else.