I'd like to see how this plays out.

At the high price he wants for the property, I'd never be able to find a buyer anyway.

But I have to imagine there are other options.What kind of jobs do you all recommend and why?

I'd probably try to suggest a combination of 5 acres with 20 units per acre and then suggest townhouses on the other 3 acres.

It will probably not positively cash flow while you are living in it (unless you make some changes that I will get to in a sec) but it would still be a win because you would be paying down a mortgage rather than renting and I imagine your monthly housing cost might end up lower, AND you will now benefit from appreciation.

They're lucky one of us doesn't live there, I can just imagine fun things to do to screw with them.Actually, have a big party and invite BP regulars, I can see it now..... :-)

I'd suggest speaking with an agent who also househacks.

I've all the questions and hesitations of a rookie as you might imagine.

I'd stick with high quality.  

I'd house hack a few times and get some equity and cash flow going over the next few years and see how that gives you more options in the future.