In either situation, you should have something in the lease to the effect that the landscaping should be in as good a condition at move out as it was at move in, so that it doesn't end up a wreck (well, eventually I think it will become a wreck because it is at a rental after all).

But the whole idea of arbitrarily 10Xing every goal in your life could be a train wreck if not handled with wisdom.  

Deep down if I'm being completely honest it's just been really nerve wrecking to even believe I can go into something new and risky.  

Wreck, drive through the garage liability....They should rent their latest and best imports with their own insurance.Put some hams, steak and best beer in the frig will you?

an hour before we were going to meet, he wrecked his car and then we both got a bit busy with life.  2 months later, I saw a deal that really stood out and emailed it to him.  

If you don't wreck it and can sell it to the next sucker, you are only out say 10-20K.

I would like to see the average carpenter/ electrician, etc, remove the front end of a car, remove the engine, straighten damaged frame rails,  cut out and replace what is needed to within a .0-.3 mm tolerance and then get it all put back together and guarantee that if there is another wreck that the air bags will go off at the right millisecond.

Painting over it can be a train wreck waiting to happen,,specially if its a 'waxy' paper.If it is really really tough to get off I do believe it is probably faster and cheaper to jerk the drywall and install new.

It can wreck your reputation as a professional.

In most cases the standard is "broom clean", but if you're buying a wreck that was occupied by a hoarder, it would most likely specify that "the buyer is responsible for disposing of building contents and cleaning".As @Russell Brazil pointed out, this is why we do a final walkthrough as close to closing as possible.