for form validation and list user i think you can do something like :

e.g. using sqlform.grid (you can modified it if you want to use sqlform)

def __onvalidation_booking(form):
    if form.vars.start_availability > form.vars.end_availability:
        form.errors.end_availability = 'End Availability must Greater than 
Start Availability'

def availability():
    query = db.user_availability.is_active==True
    grid=SQLFORM.grid(query, user_signature=False, 
                      onvalidation=__onvalidation_booking)
    return locals()

and for conditional after they have expired, set as inactive 
(is_active=False), i think you can do something like background process 
(cron jobs) to check every day/hour after the conditional is fulfilled it 
will updated the value is_active=False.

hope this can help

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