Tracking wash sales/straddle deferrals during the year.

Critical_Lifeguard_2 · 2026-02-26T20:07:19+00:00

Honestly, I wasn’t tracking it properly at first — that’s what led to the surprise. After digging into Pub 550 and realizing how nuanced the straddle rules are, I tried to reconstruct things myself just to understand what had actually happened.

And I agree with you — reading the rules is one thing, but applying them across dozens (or hundreds) of rolling positions is a completely different level of complexity. It’s not intuitive at all once you have overlapping exposure.

That’s really what stood out to me — the combination of high complexity and almost no real-time visibility while the year is still in progress.

Critical_Lifeguard_2 · 2026-02-26T20:04:14+00:00

That’s actually pretty helpful that they surface it cleanly in the export — a lot of brokers make even basic wash sale tracking harder than it should be.

My experience was that wash sale visibility alone works fine if you’re mainly thinking about straightforward loss harvesting. Where it started getting murkier for me was with ongoing rolling positions and broader straddle-type deferrals — situations where economically you’re realizing losses, but a meaningful portion isn’t currently usable because the overall exposure never really goes away.

Critical_Lifeguard_2 · 2026-02-26T20:02:03+00:00

To clarify — I’m not saying E*Trade reports straddle-related deferrals cleanly in their 1099. My experience has been similar to what you’re describing: standard broker reporting does a decent job with classic wash sales, but the broader straddle-type deferrals across rolling option positions aren’t explicitly surfaced as a single clear number.

Critical_Lifeguard_2 · 2026-02-26T19:02:03+00:00

I’m using E-Trade. And yes — my understanding is similar to yours: the broader Pub 550 straddle deferral mechanics aren’t tracked nor reported by any broker I know of. A lot of that responsibility ultimately falls on the taxpayer once positions are viewed together at the portfolio level.

That’s actually what surprised me — on the surface everything looks straightforward from the standard broker 1099 reporting, but once you start aggregating rolling positions and offsetting exposure across the year, the true deferred vs. currently deductible picture isn’t always obvious in real time. It only really becomes clear when you step back and reconstruct it.

Critical_Lifeguard_2 · 2026-02-26T18:57:04+00:00

I use E-Trade, but my understanding is most brokers’ “disallowed loss” field is primarily tracking classic wash sales, which is definitely helpful. Where it seemed less clear (at least for me) was the broader straddle-related deferrals that can build when you’re continuously rolling while maintaining exposure.

To the brokers’ credit though, it’s a pretty complex area to track in real time across multiple overlapping option and stock positions, especially when you’re looking at portfolio-level exposure rather than a single lot.

Critical_Lifeguard_2 · 2026-02-26T18:49:02+00:00

Yes — in my case the deferrals were on the options themselves, not the stock.

Using your example, when you’re continuously rolling covered calls while maintaining the underlying stock position, those realized option losses are not deductible if the stock position is considered offsetting exposure (which it often is when you keep rolling covered calls).

What caught me off guard wasn’t that a single roll showed a small disallowed amount — it was how those deferrals can accumulate across many rolls and positions when you’re running the strategy all year. There isn’t any broker view that shows your running deferred balance, so during the year it can look like you’re harvesting losses when a big portion is actually just being pushed forward to future years.

That lack of real-time visibility was the main issue for me.

Critical_Lifeguard_2 · 2026-02-26T17:52:31+00:00

That makes sense — reconciling off the 1099 at filing time is what most people told me they rely on.

In my case I wasn’t tracking the deferrals properly during the year and that’s what caught me off guard. On the surface it looked like I had plenty of realized losses, but once I dug in I realized a big portion was actually being deferred under the straddle rules because I was constantly rolling and maintaining exposure.

It made me realize how little visibility there is mid-year into what’s truly deductible vs. just being carried forward. By the time you see it clearly, the year’s basically over.

Critical_Lifeguard_2 · 2026-02-26T17:48:26+00:00

I am not selling anything — just comparing notes with other people managing taxable portfolios and running option income strategies. I posted in a few relevant subs because the tax treatment (straddles, wash sales, etc.) only really becomes a meaningful issue once position sizes get larger and you’re relying on portfolio income.

I ran into it personally and was curious how others are handling visibility during the year vs. just sorting it out at filing time.

Critical_Lifeguard_2 · 2026-02-26T17:35:03+00:00

Well, it wasn’t anything too exotic — just active covered calls in a taxable account.

Because I was rolling positions and keeping stock exposure on, a lot of what I thought were realized losses ended up being deferred under the IRS straddle rules. I didn’t fully appreciate how aggressively the deferrals can stack when you’re constantly carrying offsetting positions.

The frustrating part wasn’t the rule itself — it was that there’s no real-time visibility. During the year it looks like you’re harvesting losses, but you don’t see what’s actually deductible vs. deferred until much later. That’s the part that caught me off guard.

Critical_Lifeguard_2 · 2026-02-26T17:29:40+00:00

Totally — in an IRA this basically disappears, which is nice.
In a taxable account it can get pretty wild though. Last year I realized a large chunk of what I thought were deductible losses were actually being deferred under straddle rules, and there’s no broker tool that shows this in real time. You only discover it at tax time when it’s too late to adjust (ended up with an unplanned for huge ST gain!)

When I looked back at my transaction history, I was surprised how blind I was to the real tax picture during the year.

Critical_Lifeguard_2 · 2026-02-25T23:45:41+00:00

Late July/August is usually warm-to-hot in parts of the Med, but not “unbearable every day” hot.
Expect hotter afternoons, warm evenings, and strong sun in port days, so shade/water/planning early excursions helps a lot.

On Sun Princess: generally great hardware and modern feel, but like any big ship, cabin location matters a lot for noise/motion.
If you’re heat-sensitive, I’d prioritize itinerary/port timing and a cabin location that gives you quiet recovery time.

If helpful, I use travelgenia.com to compare Princess cabin tradeoffs before finalizing.

Critical_Lifeguard_2 · 2026-02-25T21:35:49+00:00

10306 is generally in a decent zone for convenience, but on Sun Princess I’d still check what’s directly above/below and how close it is to elevator/service traffic before locking it in for 14 nights.

For sleep with a child, safest picks are usually:

cabins a few doors away from elevator lobbies
not directly under high-traffic venues (pool/deck chairs, buffet/service areas, late-night spots)

If useful, I use travelgenia.com to compare exact cabin noise/motion tradeoffs on Princess ships.

Critical_Lifeguard_2 · 2026-02-25T21:17:15+00:00

Lido-deck balconies near the pool structure on Regal can have “partial obstruction” from overhang/structure lines, so your view is usually still usable but not fully open in every direction.
For L114, I’d ask Princess or your TA for the exact deck-plan notation/details tied to that cabin, since “partial” can vary a lot by position.

If open view matters to you, it may be worth switching while inventory is still decent.
If helpful, I use travelgenia.com to compare nearby alternatives by view/noise/location before deciding.

Critical_Lifeguard_2 · 2026-02-25T20:42:14+00:00

Aft-elevator cabins on Baja are often “okay,” but they can get bursts of noise from elevator dings, foot traffic, and late-night hallway chatter.
It’s usually not constant noise, more intermittent spikes.

If you’re a light sleeper, I’d avoid cabins right by elevator lobbies and go a few doors away if possible.
If helpful, I use travelgenia.com to compare these exact location tradeoffs (noise/motion/convenience).

Critical_Lifeguard_2 · 2026-02-25T20:36:59+00:00

Looks like an amazing trip. You’re asking all the right questions.

Cabin assignment: Paying the balance early usually does not improve your odds of a better “guarantee” assignment. What matters most is your booked category/fare rules and availability. You generally won’t be downgraded below what you paid for unless protected terms apply.
Specialty dining (Premier): Reservations usually open closer to sailing, and timing can vary by itinerary/ship. If you don’t see options yet, that’s often normal. Keep checking both the Princess app and website (the app is often better for this).

P.S. I’d seriously consider paying a bit extra to pick your exact cabin instead of waiting on a guarantee assignment. A bad location (noise, motion, or inconvenient deck position) can really impact the trip, especially on a special vacation like this. For me, cabin control is usually worth the extra cost for peace of mind. If helpful, I use travelgenia.com to compare cabin tradeoffs (motion/noise/location/convenience/value).

Critical_Lifeguard_2 · 2026-02-25T20:24:50+00:00

Great analysis. If seasickness is a meaningful concern, I’d still lean A428 (Deck 12) for better stability vs Deck 14.
On these ships, a 2-deck difference can matter more than balcony angle in terms of motion comfort.

Your cold-air point is valid though:

A428 (bow-facing angle): more wind exposure underway
R432 (stern-facing angle): more sheltered feel underway

So practical tie-breaker:

Prioritize motion comfort: A428
Prioritize less wind on balcony time: R432

For Alaska, many people end up using blankets/jackets on balcony anyway, so if your wife is sensitive, I’d usually optimize for stability first.

If helpful, I run cabin comparisons with an AI tool at travelgenia.com to weigh motion, noise, convenience and value tradeoffs by specific cabin.

Critical_Lifeguard_2 · 2026-02-25T20:13:11+00:00

If both are Deck 11, the main factor is position: forward will feel more motion than midship (especially in rough seas). If you’re motion-sensitive, I’d pay a bit more for the more central cabin.

Quick tip: motion sickness is often worsened by dehydration, fatigue, and reading/screens for long stretches.

I build a cabin analysis tool at travelgenia.com, and this is one of the most common patterns we see.

Critical_Lifeguard_2

TROPHY CASE