This issue is also the crux of my current decision and why I ended up here to investigate.

As far as making the decision on which one to go with, that answer is simple.

However, they make all the bottom line decisions like who to rent too and how much to charge. 

(its called work for a reason) So, I would tread lightly here, because, you have what some vets call: a Daisy Chain; meaning you are one step (or more) removed from the decision maker.)

The upstairs unit has been rented out for about 6 years now and last week I finally made the decision to move and now the downstairs unit is rented as well.I have equity in the home, the rental income will cover mortgage, insurance, taxes AND my son's school tuition.My next step is to finally get that first wholesale property under contract and start looking for another multi-family unit I can move into while renting out the remaining units.BTW, I am looking in Santa Cruz - so if you know of anything let me know!

I've done some checking and as long as he doesn't provide legal advice, he can guide me through the paperwork and decision making process.

I'm nervous that purchasing used appliances was the right decision, but the price was right, and we needed to make cuts somewhere to stay close to budget. 

There is more danger of making an emotional decision due to your love for this properly. don't rush and stick to your criteria for finding a deal.

Jokes would be a great way to break the ice but I'm more worried about what they don't say/think and how that'll effect their selling decision.

My preference is to determine whether the principal is aware of any such issues or just ignorant to the facts and make a decision about investing more time into a messy file.