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I solved it the following way, just want make sure I'm not missing something obvious. Set up a portfolio $PF$ consisting of long $S$ and short $P$ at time $t = 0$. Choose arbitrary time $0 < t < T$. If $S_t > P_t$ then $PF_t = S_t - P_t$ which coincides with the value of the option. If $S_t$ hits $P_t$ from above, then dissolve the portfolio by ...

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You introduce a discretized auxiliary variable which represents $S_t$ to solve $N$ PDEs on $[t, t+\tau]$ using finite differences which will give you the present value of the option at time $t$ conditional on $S_t$. Then you solve one PDE using finite differences on $[0, t]$ to obtain the the present value at time $0$. This is the same methodology than that ...

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I think it's ok $$S_T = e^{\ln S_T}$$

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There is a problem in your last step. Note that \begin{align*} P_{t, T_2}E_{Q_{T_2}}\left(\frac{1}{P_{T_1, T_2}} \mid \mathcal{F}_t \right) &= P_{t, T_2}E_{Q_{T_2}}\left(\frac{P_{T_1, T_1}}{P_{T_1, T_2}} \mid \mathcal{F}_t \right)\\ &=P_{t, T_2} \times \frac{P_{t, T_1}}{P_{t, T_2}}\\ &=P_{t, T_1}. \end{align*}

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The option payoff is equivalent to $Z_{\tau \wedge T}-1$ where $\tau=\inf\{t | Z_t = 1\}$ provided that $Z_t$ is assumed to be continuous. Since $Z_t=S_t/P_t$ is a martingale under $Q_P$, we have $E_P[Z_{\tau \wedge T}]=Z_0$ and the option value is $P_0 (Z_0 - 1)=S_0-P_0$ regardless of the model.

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The option payoff at maturity $T$ is defined by \begin{align*} (S_T-P_T)1_{\left(\inf_{0 \le t <T}\frac{S_t}{P_t}\right) > 1}. \end{align*} Let $Q$ be the risk-neutral probability measure and $E$ be the corresponding expectation operator. Let $Q_p$ be a probability measure defined by \begin{align*} \frac{dQ_p}{dQ}\big|_t = \frac{P_t}{e^{rt} P_0}. ...

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from a practitioner perspective, i can say there's no such thing as a 0 year swap (obviously). The shortest tenor that you could trade would be a contract on one month LIBOR or more likely 3 month LIBOR. Then the instrument you are asking about is a 5 year expiration caplet (payoff in 5 years = max (0, LIBOR- strike).)

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There's no best method. The question is : what is the behavior of the volatility structure (atm and skew) when the underlying moves? Each method assumes something different. In the real market, one method might work well for a period of time (in the sense that it minimizes residual p/l), but then another method might take over as best. Practitioners ...

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