My employer offers an ESPP with the following details:
- 15% discount
- Max contribution is 15% of base salary
- Purchase transaction occurs on the last business day of the month
- Transaction settles 3 days after purchase
- No obligation to hold the stock for minimum duration
- No restrictions on sell timing (except during earnings lock-out period)
- Brokerage fees
- $0.05 per share sold (approximately 0.08% of the stock price today)
- $0 per share bought
Given these parameters...
What is the safest way to play the ESPP?
What is (likely) the most lucrative way to play the ESPP?
Assume I contribute the maximum amount allowable. Assume I can hold the stock for up to you year before I may need to cash it out.