They could downsize into something in a more modest price range or even become renters so they don't have to deal with maintenance etc. 

Is this something I should even worry about? 

I will keep this positive attitude even when the going get rough :) 

Taking out a loan for EMD would make it way, way too tempting to look past issues in DD and close no matter what.I'd also be concerned about the ability to close in general if cash is too tight to fund even the EMD.

The whole tax return package was more than 300 pages, so I had to spend a few hours reviewing them, but not even one thing needed to be changed this year.

It's a smart way to reduce or even eliminate your own living expenses while gaining investment experience.

i use the Schlage lock and yes, i integrate it so that it is the last 4 of their cell. it activates 1 hour before their reservation and deactivates 1 hour after. i dont even worry about it anymore, 1 less thing i have to think about.

I'm an engineer and even then, I'm getting really tired of feeling like life is a paycheck-to-paycheck situation even being an engineer...  

It would have been a break even prospect for 10+ years.

Unless there's a tripping hazard or something like that you should be fine (and even in such cases, your insurance should cover it although they might force you to address the tripping hazard).