Something about this situation warrants a closer look before any money changes hands.
Let's take the two requests separately. Transportation upon release is something most state and federal systems actually provide. Inmates are typically given a bus ticket, a gate card with a small amount of funds, and in some cases a ride to a transportation hub at no cost to them or their families. The idea that a paroling inmate needs family to fund their own bus ticket home is not impossible but it is unusual enough to raise a flag.
Ankle monitor costs are more complicated. Some jurisdictions do charge supervised release fees that can include monitoring costs, and in certain states those fees are deducted from the inmate's account or billed after release. However, the facility handles that administratively and it does not typically require the family to send money to the inmate's books in advance as a condition of release.
The combination of an unspecified release date, a request for money, and a release that never materializes is a pattern worth taking seriously. Inmates occasionally tell family members what they want to hear about imminent release as a way of generating commissary funds.
The only way to know for certain what is real is to call the facility directly and ask to speak with the counselor handling your person's reentry. That counselor knows exactly what the actual release plan looks like, what costs if any are the inmate's responsibility, and whether a release date has been set. Five minutes on that call tells you more than any amount of back and forth with your family member inside.