SQL Server 2017

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declare @Job TABLE (id INT, userid INT)
INSERT INTO @Job ( id ,userid) VALUES  ( 1,1)
INSERT INTO @Job ( id ,userid) VALUES  ( 2,1)
INSERT INTO @Job ( id ,userid) VALUES  ( 3,2)
INSERT INTO @Job ( id ,userid) VALUES  ( 4,2)
INSERT INTO @Job ( id ,userid) VALUES  ( 5,1)

declare @User table (id INT, UserName NVARCHAR (30))
INSERT INTO @User ( id ,UserName) VALUES  ( 1,'Richard')
INSERT INTO @User ( id ,UserName) VALUES  ( 2,'Jane')

declare @Estimate table (id INT, [job] INT, [GrossValue] DECIMAL (18,2))
INSERT INTO @Estimate ( id ,[job], GrossValue) VALUES  ( 1,3, 100)
INSERT INTO @Estimate ( id ,[job], GrossValue) VALUES  ( 2,4, 100)
INSERT INTO @Estimate ( id ,[job], GrossValue) VALUES  ( 3,5, 200)
INSERT INTO @Estimate ( id ,[job], GrossValue) VALUES  ( 4,5, 200)

declare @AdditionalEstimate Table (id INT, [job] INT, [GrossValue] DECIMAL (18,2))
INSERT INTO @AdditionalEstimate ( id ,[job], GrossValue) VALUES  ( 1,1, 100)
INSERT INTO @AdditionalEstimate ( id ,[job], GrossValue) VALUES  ( 2,2, 100)
INSERT INTO @AdditionalEstimate ( id ,[job], GrossValue) VALUES  ( 3,5, 100)
INSERT INTO @AdditionalEstimate ( id ,[job], GrossValue) VALUES  ( 4,5, 100)

declare @Order table (id INT, [job] INT, ContractGiven DECIMAL (18,2), InvoicesReceived DECIMAL (18,2))
INSERT INTO @Order ( id ,[job], ContractGiven,InvoicesReceived) VALUES  ( 1,1, 50, 0)
INSERT INTO @Order ( id ,[job], ContractGiven,InvoicesReceived) VALUES  ( 2,2, 150, 0)
INSERT INTO @Order ( id ,[job], ContractGiven,InvoicesReceived) VALUES  ( 3,3, 50, 0)
INSERT INTO @Order ( id ,[job], ContractGiven,InvoicesReceived) VALUES  ( 4,4, 150, 0)
INSERT INTO @Order ( id ,[job], ContractGiven,InvoicesReceived) VALUES  ( 5,5, 400, 0)
INSERT INTO @Order ( id ,[job], ContractGiven,InvoicesReceived) VALUES  ( 6,5, 100, 0)

select J.id [Job]
  , coalesce(O.InvoicesReceived,0) InvoicesReceived
  , coalesce(O.ContractGiven,0) ContractGiven
  , coalesce(E.GrossValue,0) + coalesce(A.GrossValue,0) TotalQuoteCost
from @Job J
left join (select Job, SUM(O.InvoicesReceived) InvoicesReceived, SUM(O.ContractGiven) ContractGiven from @Order O group by Job) O on O.Job = J.id
left join (select Job, SUM(E.GrossValue) GrossValue from @Estimate E group by Job) E on E.Job = J.id
left join (select Job, SUM(A.GrossValue) GrossValue from @AdditionalEstimate A group by Job) A on A.Job = J.id
where (
  coalesce(O.InvoicesReceived,0) > (coalesce(E.GrossValue,0) + coalesce(A.GrossValue,0))
) OR ( 
  coalesce(O.ContractGiven,0) > (coalesce(E.GrossValue,0) + coalesce(A.GrossValue,0))
)

select [User Name], count(*)
from (
  select U.UserName [User Name], J.id
    , coalesce(O.InvoicesReceived,0) InvoicesReceived
    , coalesce(O.ContractGiven,0) ContractGiven
    , coalesce(E.GrossValue,0) + coalesce(A.GrossValue,0) TotalQuoteCost
  from @Job J
  inner join @User U on U.id = J.UserId
  left join (select Job, SUM(O.InvoicesReceived) InvoicesReceived, SUM(O.ContractGiven) ContractGiven from @Order O group by Job) O on O.Job = J.id
  left join (select Job, SUM(E.GrossValue) GrossValue from @Estimate E group by Job) E on E.Job = J.id
  left join (select Job, SUM(A.GrossValue) GrossValue from @AdditionalEstimate A group by Job) A on A.Job = J.id
  where (
    coalesce(O.InvoicesReceived,0) > (coalesce(E.GrossValue,0) + coalesce(A.GrossValue,0))
  ) OR ( 
    coalesce(O.ContractGiven,0) > (coalesce(E.GrossValue,0) + coalesce(A.GrossValue,0))
  )
) x
group by [User Name]

INSERT INTO @Order ( id ,[job], ContractGiven,InvoicesReceived) VALUES  ( 7,2, 350, 0)
INSERT INTO @Order ( id ,[job], ContractGiven,InvoicesReceived) VALUES  ( 8,2, 150, 0)

Job	InvoicesReceived	ContractGiven	TotalQuoteCost
2	0.00	150.00	100.00
4	0.00	150.00	100.00

User Name	(No column name)
Jane	1
Richard	1

Job	InvoicesReceived	ContractGiven	TotalQuoteCost
2	0.00	650.00	100.00
4	0.00	150.00	100.00

User Name	(No column name)
Jane	1
Richard	1