Roll Up-and-Out Twilio Inc. Cash-Secured Put Position

On May 17th, the Covered Calls Advisor established a 100% Cash-Secured Put position in Twilio Inc. at the June 18th, 2021 $270.00 strike price.  Twilio shares have spiked higher from $289.04 when this position was established to $332.60 today, so the Covered Calls Advisor decided to roll-up-and-out from the $270.00 strike price to the $300.00 strike price at the June 25th, 2021 options expiration date.  A vertical credit spread transaction was executed at a net credit of $4.42 ($5.40 - $.98) per share.  There was only $.98 time value remaining in the $270.00 Calls for the next 24 days and trading up to the $300.00 Put added $4.42 to the remaining time value.

A potential return-on-investment result for this Twilio Inc. Cash-Secured Put position is +5.5% absolute return in 40 days (equivalent to a +50.0% annualized return-on-investment) if the stock price closes above the $300.00 strike price on the June 25th options expiration date. 
By rolling up the original position, this result would exceed the +3.8% absolute return (+41.8% annualized) that was the maximum potential of the original Cash-Secured Put position at the $270.00 strike price.  The blog post detailing this original position is here.   The detailed transactions and a potential result are provided below.    

Twilio Inc. (TWLO) -- New 100% Cash-Secured Put Position
The original transaction was as follows:
05/17/2021  Sold 1 Twilio Inc. June 18th, 2021 $270.00 100% Cash-Secured Put options @ $9.85 per share.
Note: the Implied Volatility of this Put option was 52.3 when this position was transacted.
05/26/2021 Roll up transaction executed:
Bought-to-Close 1 TWLO 6/18/2021 $270.00 Put option @ $.98 per share and simultaneously Sold-to-Open 1 TWLO 6/25/2021 $300.00 Put option @ $5.40 per share
Note: The estimated probability that this $300.00 Put option closes out-of-the-money (stock price above the strike price) on the June 18th options expiration date was approximately 80% when this roll up transaction was executed.

The Covered Calls Advisor does not use margin, so the detailed information on this position and the potential result detailed below reflect that this position was established using 100% cash securitization for the one Put option sold.

A possible overall performance result (including commissions) would be as follows:
100% Cash-Secured Put Cost Basis: $26,015.67
= ($270.00 - $9.85) * 100 shares + $.67 commission

Net Profit:
(a) Option Income: +$1,424.99
= ($9.85 - $.98 + $5.40) * 100 shares - $2.01 commissions
(b) Dividend Income: +$0.00
(c) Capital Appreciation (If Twilio stock is above $300.00 strike price at the June 25th expiration): +$0.00
= ($300.00 - $300.00) * 100 shares

Total Net Profit (If Twilio stock price is out-of-the-money (above $300.00 strike price) on the June 25th options expiration date): +$1,424.99
= (+$1,424.99 option income +$0.00 dividend income + $0.00 capital appreciation)

Absolute Return (If Twilio is above $300.00 strike price at the June 25th, 2021 options expiration) : +5.5%
= +$1,424.99/$26,015.67
Annualized Return: +50.0%
= (+$1,424.99/$26,015.67) * (365/40 days)