The house with the orderly in the yard...

[skyks78]

I've often wondered about this...there is a house in the Vale where, when you enter the yard, a man dressed identically to an orderly from Happy Volts will chase you.  Any theories? 
I

[deadpoolXYZ]

It's the retirement home for old people. You aren't allowed in that area unless you are using the orderly uniform just like in the asylum. Theo the orderly is patrolling the area and you can find a rubberband.

Bully wiki:

Happy Endings Retirement Home

Set in the middle of the residential area of Old Bullworth Vale, the retirement home is home to a few elderly but well to do citizens. Trespassers are not allowed on the grounds, and the area is patrolled by the orderly Theo. There is a dry pond bed on the grounds with a bridge over it, and a Rubber band collectable under the bridge.

[Owais Qadri]

I'm gonna go in there when I play bully again

[BloodChuckZ]

Well, here's the thing.  Old People are walking around the yard, so Theo is there to protect them.

Now, there is a spot on the wall around back (there is some fencing laying against it on the street side), where you can stand on the wall and attack from, with your weapons without being busted. 

[SWEGTA]

Occasionally, a greaser will spawn there and egg the house. So it makes sense having Theo (the orderly) there to guard the place.

[Owais Qadri]

Yes it makes sense gonna go on bully later and research all these myths

[skyks78]

Hmm is it the same orderly from Happy Volts? 
 And why does Miss Abby live in a crappy tenement building and not the home (maybe I'm putting too much thought into this...

[Owais Qadri]

There is some creepy some stuff in bully

[BloodChuckZ]

Hmm is it the same orderly from Happy Volts? 
 And why does Miss Abby live in a crappy tenement building and not the home (maybe I'm putting too much thought into this...

Probably as in real life, it's a money issue.  Or, could be that many old people would rather live in their homes rather than be warehoused in some facility.