My fear is that at this age buildings will lose value even if renovations and repairs are up to date.

I also just want to make sure I am ready to go when these deals become more prevalent, which is why I would like to start building relationships now, with who is willing to take a chance :)

Like in the BP podcast #635 one thing it talks about is getting over the initial fear and acting fast.  

Even if you make a mistake, just hang on and time will likely erase that mistake.Proverbs 9:10 The fear of the Lord is the beginning of wisdom.

With ADUs I have seen valuations all over the place (I have not figured them out) but the one that seems to be most prevalent is to have the ADU add $50k to $80k then subtract for any subtractions (in your case the loss of the garage would subtract from the value they assign for the ADU) with a primary factor being how much the units appear to be unrelated.  

And I must admit, that even though we have made a few good choices, we still fear losing everything we have.

I think the biggest risk would be your fear of enforcing the lease because it may negatively affect your standing as a student.

Having enough savings to launch yourself into a new career path with better income potential without having the fear of not being able to make ends meet.

We then made a reasonable offer on the amount of funding and the cost of our capital based on the risk factors that we saw prevalent at the time.How did you finance this deal?

The only thing I can add is that for a short amount of time, I think sellers were fearful that their home wouldn't sell and it was easy to negotiate more in credits but again, still holding up pretty strong here!