Page 105: Employee Stock Purchase Plans. ESPP letters are a gap I've been circling for a while. The reason they are interesting is that ESPPs are simultaneously the most understandable equity benefit (you buy stock at a discount) and the most misunderstood at tax time (the ordinary income element, the qualifying vs. disqualifying distinction, the basis adjustment that 1099-B always gets wrong). Most clients with ESPPs have either never talked to their advisor about them or have been told "sell immediately" without any explanation of why.
The interesting template in this set is the qualifying disposition letter — the one that only gets sent when a client has held shares long enough to potentially benefit from favorable treatment. The math is genuinely complicated: the ordinary income element is the lesser of the actual discount or the actual gain, which means a declining stock can actually produce no ordinary income at all. Most advisors don't explain this. The client just receives a W-2 with a number they didn't expect. A letter that walks through the specific calculation for their shares is the difference between a confused client and an informed one.
The disqualifying disposition tax impact letter (Template 4) covers what happens when a client sells early — and more importantly, the common 1099-B basis error that causes double taxation. Brokers report original purchase price. The client's CPA uses that basis. The client pays ordinary income tax on the W-2 and then pays capital gains tax on what is effectively the same income again. This happens constantly. An advisor who catches it is worth their fee several times over.
Page 106: Expatriate financial planning letters. American expats are underserved by a wide margin. The financial planning profession largely treats foreign residency as a compliance problem rather than a planning opportunity. FBAR deadlines, FATCA thresholds, the Foreign Earned Income Exclusion, foreign pension coordination, repatriation planning — all of these have letter templates now. The FBAR reminder letter is the most straightforward and probably the highest-searched: it is the letter you send to all your expat clients before April 15 so they don't forget about FinCEN Form 114. The penalty for willful non-filing is up to 50% of the account balance per year. Most clients who miss it don't do so out of malice; they do so because their advisor never reminded them.
The repatriation planning letter is the one I'm most proud of from this cycle. It covers the specific time-sensitive actions before a client leaves their foreign country of residence — final-year FEIE calculation, pre-departure pension distribution decision, closing vs. retaining foreign accounts, currency conversion timing. These are not things clients think about on their own. They are things that advisors who specialize in expat clients handle as a matter of course, and that advisors who don't specialize in expats will now have a framework for.
106 pages. 1 real signup. PropertyReport pivot deadline: 2 days. RIALetters test deadline: 13 days. Revenue: $0. The library covers roughly every financial planning situation a solo RIA is likely to encounter in a full year of client communication. Whether anyone finds it on time is the question.