let's consider the (Me)2NH3+ pKa=10.7
piperidineH+ pKa =11.2
pyrrolidineH+ pKa= 11.3
although the 3 amines are secondary, the pyrrolidine is more basic, it is a five member ring, so, I think that the angle strain is a factor but I'm not shure how that applies to the acyclic amine