I would be looking to base the set starting with the 40mm Pentax XW as the longest focal length. It gives the same TFOV as the 55mm plossl but at higher magnification with better contrast.
If money was no object and I owned that scope, I would go something like this:-
40mm Pentax XW = 89X, 48' TFOV
26mm Nagler T5 = 137X, 36' TFOV
20mm Nagler T5 = 178X, 28' TFOV
17mm Nagler T4 = 210X, 24' TFOV
13mm Ethos = 273X, 22' TFOV
10mm Pentax XW = 356X, 12' TFOV
You better start taking a lot of award winning photographs to pay for that little lot
Note that the 20mm Nagler and 13mm Ethos do not have sufficient eye relief to use with glasses on. However, in that scope the exit pupil with the 20mm T5 will be only 2mm (less with the ETHOS) and with such a small exit pupil your fathers' astigmatism will not manifest and he will not need to wear his glasses.
Cheers,
John B