This might give a one-time (non-scalable) boost to cash flow, offer multiple value-add options, and allow the house-hacker peace of mind, via the assumed mortgage, in long-term breakeven or positive cash flow in the event that the value-add plans end up not being executed, and/or the person has to move out, and rent by the room or STR become unavailable for some reason at a future date.

This person has 8 months remaining on their lease.

Offered to intern/work for him at half the pay as his personal assistant if he would teach me everything he knew.

I don't have personal experience with it, but when the app was first developed, I contacted the developer and put the app through a fairly robust test usage to see if it's something I would want to recommend to my clients (I'm a CPA).I think the app is great for its intended purpose and I do recommend it to my clients now (and have for about 18 months now). 

A realtor doing high volume, you don't have to use one you can poll 3-5 agents see what they do to get you the comps and then pick that person to help you.

There are many resources for you to connect online and in person.

Do you own a personal residence yet?

@Dustin Horner you should be contracting maintenance work and creating a preferred list of vendors as @Phillip Austin has recommended.The first person you hire to help you should be to handle what you LEAST like to do yourself or has the greatest time savings for you!

I am looking at a 5 unit building that I want to do a condo conversion on. 4 units would be vacant 1 has a rent controlled tenant in there who does not want to move. I would owner occupy it so I don't know if I have a...

Would even be happy to meet in person since we are in the same area.