Hopefully he has also seen you deliver at work, and your willingness to roll up your sleeves and take on a task, without hesitation.many potential investors show up at meetups but fail to follow through or even have a plan.I'd suggest you take this further by developing a business plan and goal setting. 

I am looking forward to this new adventure. 

I have settled on the strategy of house-hacking to start off my adventure with the incredible power it can have of reducing expenses to free up for more investments and focusing my research on this niche per Brandon’s principles.My plan was to simply watch and wait.

Roughly calculate your hourly comp rate for last year, estimate hours per project tasks, a rough calculation for getting to your "number" then decide how much leverage you have to ask for it as guaranteed fees vs. risk as profit sharing contingency, etc.

Your vision is very similar to my vision, execpt I‘d like to own in adventure sport paradises.

The most difficult task I foresee for myself is just finding a tenant, screening, showings, and placing the tenant in the home as I'll be living about 1.5 hours away (2+ hours pending the Los Angeles traffic) and work a full time job.

This contractor had a very specific task that they essentially defined. 

Not to burst your bubbles, but finding a 4-plex is a bit of a task in A-town. 

It seems that it takes the headache out of a lot of the daily monotonous tasks. 

There are also specialty tradespeople who have skills in specific tasks like plumbers and electricians.