Let us consider a payment schedule $\mathcal{P}:=\{t_1,\dots,t_n\}$ which has a corresponding fixing schedule $\mathcal{F}:=\{t_0,\dots,t_{n-1}\}$. We have a series of co-terminal and co-initial swaps with coinciding float and fixed payment dates, accrual conventions and notionals $-$ the specific float rate does not matter. Hence the value of these swaps at time $t$ are in the case of a payer: $$V_t(t_i,t_j)=\sum_{k=i}^j\delta_k(R_t(t_{k-1},t_k)-C)P_t(t_k)$$ where $C$ is the swap fixed rate, $R_t(t_{k-1},t_k)$ the forward value of the float rate fixing at $t_{k-1}$ and paid at $t_k$, and $P_t(t_k)$ the discount factor, with $\delta_k:=t_k-t_{k-1}$ the accrual fraction (we have dispensed with notional and assumed it is 1).
Let us introduce the notation $\mathcal{F}_{i,j}:=\{t_i,\dots,t_j\}$. Let $B_t(t_i,t_n)$ be the value at $t$ of a vanilla Bermudan swaption which gives the right to enter on one of the fixing dates $t_{i-1},\dots,t_{n-1}$ into a swap starting (payments) at $t_i,\dots,t_n$ respectively and ending at $t_n$, i.e. the exercise set of the Bermudan is $\mathcal{F}_{i-1,n-1}$. Let $A_t(t_i,t_n)$ be the corresponding vanilla American swaption value which can be exercised on any date within $[t_{i-1},t_n]$(1). We use equivalent notation for co-initial swaptions: $B_t(t_1,t_i)$ which can be entered on any dates from $\mathcal{F}_{0,i-1}$; and $A_t(t_1,t_i)$ where in this case the American swaption can be exercised within $[t_1,t_i]$(1).
Under which circumstances would we have:
$$\begin{align} &1)& A_t(t_{i-1},t_n)-A_t(t_i,t_n) & \ \pmb{>}\ %\quad \begin{array}\\>\\\geq\\=\end{array} \quad B_t(t_{i-1},t_n)-B_t(t_i,t_n)\ ? \\[6pt] &2)& A_t(t_1,t_{i+1})-A_t(t_1,t_i) & \ \pmb{>}\ %\quad \begin{array}\\>\\\geq\\=\end{array} \quad B_t(t_1,t_{i+1})-B_t(t_1,t_i)\ ? \end{align}$$ namely the change in value from including an additional swap flow is strictly greater for American than Bermudan swaptions?
(1) If the American swaption is exercised at $t\in[t_i,t_{i+1})$, we assume the fixing from $t_i$ accrues linearly from $t$ to $t_{i+1}$ and is paid at $t_{i+1}$. For mathematical purposes this ensures the swap value can be represented as a continuous function.