Shiff based Linear Hydrogen Bonded Liquid Crystalline homologues, viz., (4)PyBD(4(I))BrA-nOBAs for n = 2,3,4,5,6,7,8,10,11 and 12 are synthesized. H-1-NMR and C-13-NMR studies confirm the formation of HBLC and IR confirms the linear hydrogen bonding. Liquid crystal phase abundance, transition temperatures, enthalpy and order of transition are investigated by Polarized Optical Microscopy textural studies and Differential Scanning Calorimetry. Nematic, Smectic-A, -D, -C, B-hexatic, -B-Crystal, -F, -I and -G phases are identified. Large LC phase variances, viz., NAB(hex)FG and NACFG are exhibited by intermediate chain length with n = 5 and 6. A-C transition exhibited unique II-order nature. II-order nature for G-Solid transition explained. Phase diagram drawn with flexible chain length infers INA, and ACF and CIF MultiCritical Points and Lifshitz behaviour. NA TriCiritical Point predicted in [3+7] binary. Influences of chain length, linear HB and end polar(-Br) substitution for LC phase stability are is discussed. Results of Phase stability are discussed in the wake of the body of the data and reports in other LCs. DSC enthalpy suggests for utility of intermediate and higher homologues for device savvy tilted Smectic LC phases.