Answers to Questions Nos. 1 and 2. Under the Fair Housing Act ("the Act") landlords are required to make reasonable accommodations to the rented facilities and common areas, if so requested by a handicapped tenant or their legal occupant. This law applies to the use of assistance animals.
A "reasonable accommodation" is a reasonable change, exception or adjustment to a rule, policy, practice or service that will enable a handicapped person to have an equal opportunity to use and enjoy the rented facilities and common areas. There must be an identifiable relationship between the requested accommodation and the person's disability. Landlords are not required to make requested accommodations if doing so would impose an undue financial or administrative burden upon them or fundamentally alter the nature of the landlord's operations. In order to address the request, Landlords are entitled to obtain information that is necessary to evaluate it for a reasonable accommodation. With respect to a person, a "handicap" means: (a) one with a physical or mental impairment which substantially limits one or more major life activities; (b) one with a record of such impairment; or (c) one who is regarded as having such an impairment. Juvenile offenders, sex offenders, persons who illegally use controlled substances and those with a disability whose tenancy would constitute a direct threat to others, or result in substantial physical damage to the property of others, are generally not protected under the Act. If the landlord refuses a requested accommodation, the requester is encouraged to have a discussion with the landlord concerning an alternative accommodation. This is a summary only and not intended to constitute legal advice. For more information, landlords, tenants and legal occupants of tenants are encouraged to consult with their attorney or a Fair Housing expert if they have any questions regarding their rights and responsibilities.
Note: MHCO has Form No. 15 which permits residents to make reasonable accommodation requests.
I think my first step (which may have already occurred prior to the rule changes, is determine the extent of the problem for emergency vehicles along the narrow streets. Does a single car slow or restrict access to emergency vehicles? In short, how problematic is it for a single car to be parked along the street? Does it create any danger to the community, its drivers, or the emergency vehicles? Once you have that baseline, you will have a sense about the safety of making a reasonable accommodation by permitted on-street parking.
Secondly, if I were to permit anyone to park on the street (assuming the safety issue is properly vetted), I think I would insist that they have a handicapped parking permit. That way, anyone parking on the street without a permit would be easier to spot. (Although you should consider whether the permit is expired or being abused, or in the name of the car's owner.)
The handicapped caretaker is not your direct responsibility - she was hired by your resident. I do not believe convenience is the litmus test here - it's whether the rule prevents her from performing her tasks, and coming and going to the site. I think the biggest problem, and one you've not mentioned but certainly are thinking, is this could become a slippery slope. The more cars you permit to park on the street, the more others will try the same thing. At this point, I believe I'd take the position that if the parking area can accommodate two cars, then that's where they should park - even if it means shuffling them around, handicapped or not.
I do not believe handicapped caretaker has standing to request a reasonable accommodation, since he/she is not a tenant or occupant of the home. But I have not research this issue; you should verify this with your own attorney.
As for the non-handicapped caretaker, a little walk to and from the guest parking is not the end of the world. "Convenience" for a non-handicapped person is not a basis for a reasonable accommodation under the ADA, Fair Housing law, or common sense.