With regard to the halfway house question: it depends on whether medical care is provided as part of the cost of the halfway house.
Many sober living facilities are purely residential and any therapeutic value, provided by other residents in community, is incidental. It is my opinion that rent or dues paid to such a facility are not deductible.
If, however, a halfway house is operated as a medical facility and services are provided by a therapist, counselor, or other professional, the expenses related to the therapy are deductible as medical expenses, subject to the limitations described below.
Please feel free to post any additional details or questions in the comment section.
According to the IRS:
You can include in medical expenses amounts you pay for an inpatient's treatment at a therapeutic center for alcohol addiction. This includes meals and lodging provided by the center during treatment.
You can also include in medical expenses amounts you pay for transportation to and from Alcoholics Anonymous meetings in your community if the attendance is pursuant to medical advice that membership in Alcoholics Anonymous is necessary for the treatment of a disease involving the excessive use of alcoholic liquors.
You can include in medical expenses amounts you pay for an inpatient's treatment at a therapeutic center for drug addiction. This includes meals and lodging at the center during treatment.
https://www.irs.gov/publications/p502/ar02.html#en_US_2016_publink1000178889
This "definition" of halfway house if from an IRS memorandum. It relates to a halfway house as part of the penal system. Any question in TurboTax will refer to this definition as it relates to income earned within the penal system not qualifiying for Earned Income Credit. This doesn't appear to be your situation.
"With respect to individuals transferred to a halfway house, those individuals have not been released from their sentences, can be returned to the prison facility, and are usually required to perform services. Although these individuals are not confined to a prison, jail, or penitentiary, they are confined to the halfway house for the remainder of their sentence. Thus, a halfway house falls within the general definition of a penal institution. Accordingly, any amounts received for services performed by an inmate while at a halfway house are amounts received for services performed while at a penal institution. Those amounts are excluded from the definition of earned income under section 32(c)(2)(B)(iv) of the Code."
https://www.irs.gov/pub/irs-sca/1998-049.pdf
