There are 40 homeowners who would rather drag that couple through legal hell out of spite than pay a $1 parking fee. And they have the wherewithal in spades to do it.
Even if the couple gets passed all that, the homeowners are going to complain about every little thing. Crack in street? Fix it. Curb crooked? Fix it. Someone illegally parked? Deal with it now. Trash on street? Clean it. Leaves on street? Sweep it now. Grass too long? Mow it immediately. Don't answers these calls immediately? Get accused of negligent landlord.
If the couple thought they could just kick their feet back and collect checks... I just don't know what to say...
Why pay lawyers here? Spite?
If I thought I could successfully "flip" it for, say $500K, which is pocket change for the affected people in that neighborhood, then sure, $190K would be a bargain. And if the 40 property owners could kick in $20K each to sue the investor, surely they'd rather kick in $10K each to buy the street back instead.