We report on nine wide common proper motion systems containing late-type M, L, or T companions. We confirm six previously reported companions, and identify three new systems. The ages of these systems are determined using diagnostics for both stellar primaries and low--mass secondaries and masses for the secondaries are inferred using evolutionary models. Of our three new discoveries, the M3+T6.5 pair G 204-39 and SDSS J1758+4633 has an age constrained to 0.5-1.5 Gyr making the secondary a potentially useful brown dwarf benchmark. The G5+L4 pair G 200-28 and SDSS J1416+5006 has a projected separation of ~25,000 AU making it one of the widest and lowest binding energy systems known to date. The system containing NLTT 2274 and SDSS J0041+1341 is an older M4+L0 (>4.5 Gyr) pair which shows Halpha activity in the secondary but not the primary making it a useful tracer of age/mass/activity trends. We find a resolved binary frequency for widely-separated (> 100 AU) low--mass companions (i.e. at least a triple system) which is at least twice the frequency found for the field ultracool dwarf population. The ratio of triples to binaries and quadruples to binaries is also high for this sample: 3:5 and 1:4, respectively, compared to 8-parsec sample values of 1:4 and 1:26. The additional components in these wide companion systems indicates a formation mechanism that requires a third or fourth component to maintain gravitational stability or facilitate the exchange of angular momentum. The binding energies for the nine multiples discussed in this text are among the lowest known for wide low-mass systems, suggesting that weakly bound, low--to--intermediate mass (0.2M_sun < M_tot <1.0M_sun) multiples can form and survive to exist in the field (1-8 Gyr). Comment: 62 pages, 12 figures, 11 Tables, AJ accepted for publication