TWA hotel is convenient (although you still need to take the Airtrain from T8 to T5 which is circa 15/20 mins with walking time) but expensive for what you get. TWA is the optimum money no object option.

Airport hotels in Jamaica (Hilton, Garden Inn, Crowne Plaze, Hampton, Courtyard etc) usually have free shuttle service from Federal Circle but the transfer time is quite slow. In terms of value for money and speed one of the airport hotels in Jamaica with Uber (10min ride) each way isn't much different overall transfer time compared to the TWA but probably $150/200 cheaper even allowing for an Uber both ways.