Hello
I'd keep Master table as simple as possible so that each record corresponds to single service order. Using such scheme, it is relatively easy to build a summary table as you describe.
E.g.,
Master
A1 customer
A2 John Test
A3 John Test
A4 John Test
A5 Jane Test
A6 Jane Test
A7 Jane Test
B1 service
B2 Spring Cleaning
B3 Weekly Mow & Trim
B4 Hedge Trim
B5 Spring Cleaning
B6 Weekly Mow & Trim
B7 Hedge Trim
C1 charge
C2 175
C3 40
C4 455
C5 225
C6 45
C7 390
D1 hired?
D2 TRUE
D3 TRUE
D4 TRUE
D5 FALSE
D6 TRUE
D7 TRUE
E1 done?
E2 FALSE
E3 FALSE
E4 TRUE
E5 FALSE
E6 FALSE
E7 FALSE
F1 index
F2 =IF(AND(D2,NOT(E2)),A2&"|"&COUNTIFS(A$2:A2,A2,D$2:D2,TRUE,E$2:E2,FALSE),"")
F3 =IF(AND(D3,NOT(E3)),A3&"|"&COUNTIFS(A$2:A3,A3,D$2:D3,TRUE,E$2:E3,FALSE),"")
F4 =IF(AND(D4,NOT(E4)),A4&"|"&COUNTIFS(A$2:A4,A4,D$2:D4,TRUE,E$2:E4,FALSE),"")
F5 =IF(AND(D5,NOT(E5)),A5&"|"&COUNTIFS(A$2:A5,A5,D$2:D5,TRUE,E$2:E5,FALSE),"")
F6 =IF(AND(D6,NOT(E6)),A6&"|"&COUNTIFS(A$2:A6,A6,D$2:D6,TRUE,E$2:E6,FALSE),"")
F7 =IF(AND(D7,NOT(E7)),A7&"|"&COUNTIFS(A$2:A7,A7,D$2:D7,TRUE,E$2:E7,FALSE),"")
Work Order
A1 customer
A2 John Test
A3 Jane Test
B1 Service 1
B2 =IFERROR(INDEX(Master::$B,MATCH($A2&"|"&INT(COLUMN()/2),Master::$F,0),1),"")
B3 =IFERROR(INDEX(Master::$B,MATCH($A3&"|"&INT(COLUMN()/2),Master::$F,0),1),"")
C1 done?
C2 FALSE
C3 FALSE
D1 Service 2
D2 =IFERROR(INDEX(Master::$B,MATCH($A2&"|"&INT(COLUMN()/2),Master::$F,0),1),"")
D3 =IFERROR(INDEX(Master::$B,MATCH($A3&"|"&INT(COLUMN()/2),Master::$F,0),1),"")
E1 done?
E2 FALSE
E3 FALSE
F1 Service 3
F2 =IFERROR(INDEX(Master::$B,MATCH($A2&"|"&INT(COLUMN()/2),Master::$F,0),1),"")
F3 =IFERROR(INDEX(Master::$B,MATCH($A3&"|"&INT(COLUMN()/2),Master::$F,0),1),"")
G1 done?
G2 FALSE
G3 FALSE
Notes.
Formula in Master::F2 can be filled down.
Formula in 'Work Order'::B2 can be filled (copied) across columns B, D and F.
'Work Order' table shows services for each customer of which status in Master is hired but not done.
'Work Order' table's columns C, E and G are for field input and not linked to Master::E.
Tables are built with Numbers v2.
Good luck,
H