Múltiples no existen en MYSQL para verificar el recuento de filas

select
    o.*,
    SUM(if(ol.status = "Approved" and (ol.end_date > now() or end_date is null), 1, 0)) as cond1,
    SUM(if(ol.status = "Pending" and (ol.end_date != now() or end_date is null), 1, 0)) as cond2
from
    outreach o
left join 
    outreach_links ol on ol.outreach_id = o.id
group by
    o.id
having
    cond1 = 0 and cond2 != 1
;

No estoy seguro de si eso es lo que está buscando, pero puede intentarlo.