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Tax Strategist?

Posted on 3/24/26 at 3:59 pm
Posted by Neauxla
New Orleans
Member since Feb 2008
34808 posts
Posted on 3/24/26 at 3:59 pm
Can anyone recommend a tax strategist? W-2 earner but looking for legal ways to pay uncle sam less and I know my options are limited. STR vs LTR, etc. etc.

Posted by horsesandbulls
Destin, FL
Member since Jun 2008
5235 posts
Posted on 3/24/26 at 5:38 pm to
Make less money.
Posted by LSUFanHouston
NOLA
Member since Jul 2009
41733 posts
Posted on 3/24/26 at 10:33 pm to
quote:

W-2 earner


Makes it tough

Mega backdoor helps tomorrow not today

quote:

STR


Hard to pull off when you are a

quote:

W-2 earner
Posted by Penn
Jax Beach
Member since Jan 2008
23713 posts
Posted on 3/25/26 at 6:29 pm to
Not true if you willing to put up with an airbnb
Posted by LSUFanHouston
NOLA
Member since Jul 2009
41733 posts
Posted on 3/25/26 at 6:49 pm to
quote:

Not true if you willing to put up with an airbnb


Even with that, there are still hour requirements that pretty much mean you have to do all of the work yourself. Do your own bookings, cleaning, maintenance, etc.

Want to do all that? Yeah it can work. But it’s tough and hard to pull off, not impossible.
This post was edited on 3/25/26 at 6:50 pm
Posted by RIPMIKEVI
Baton Rouge
Member since Oct 2016
45 posts
Posted on 3/26/26 at 7:59 am to
STR doesn’t have hour requirements.
Posted by KWL85
Member since Mar 2023
3995 posts
Posted on 3/26/26 at 8:22 am to
quote:

Even with that, there are still hour requirements that pretty much mean you have to do all of the work yourself. Do your own bookings, cleaning, maintenance, etc.


Don't think this is accurate. I own a str. This never came up with my tax guy.
Posted by LSUFanHouston
NOLA
Member since Jul 2009
41733 posts
Posted on 3/26/26 at 8:38 am to
quote:

Don't think this is accurate. I own a str. This never came up with my tax guy.


This is what I do for a living.

A lot of rules are broken every day.

You need to spend at least 100 per year on it… and more hours than anyone else. Or 500 total hours regardless of anyone else.

Also the hours must be documented.

Good news is IRS doesn’t have capacity to audit this, so if you are breaking rules, you probably aren’t getting caught…
Posted by LSUFanHouston
NOLA
Member since Jul 2009
41733 posts
Posted on 3/26/26 at 8:40 am to
quote:

STR doesn’t have hour requirements.


It absolutely does unless you are providing substantial services, which unless you are providing meals or concierge services, you are not doing.
Posted by el Gaucho
He/They
Member since Dec 2010
60311 posts
Posted on 3/26/26 at 8:43 am to
quote:

looking for legal ways to pay uncle sam less

Why do you hate Israel
Posted by Weekend Warrior79
Member since Aug 2014
22309 posts
Posted on 3/26/26 at 8:52 am to
quote:

You need to spend at least 100 per year on it… and more hours than anyone else. Or 500 total hours regardless of anyone else.

Is this specific to STR, rental property, or just any passive income as a whole?
Posted by KWL85
Member since Mar 2023
3995 posts
Posted on 3/27/26 at 3:09 pm to
Interesting. Thanks for sharing. Guess my tax guy knows me well. I don't go out of my way to break rules, but definitely feel I pay more than my fair share.
Posted by Penn
Jax Beach
Member since Jan 2008
23713 posts
Posted on 3/27/26 at 7:41 pm to
100 hours is easy to hit
Don’t know why this is even a discussion
Posted by SquatchDawg
Cohutta Wilderness
Member since Sep 2012
20652 posts
Posted on 3/27/26 at 10:20 pm to
quote:

This is what I do for a living.

A lot of rules are broken every day.


This.

We have close friends that do backdoor Roth conversions every year even though they have legacy IRAs from prior jobs they don’t consider. Accountant said “nah…that’s fine”.

Got another buddy with a self directed IRA that does all kinds of shite that to my knowledge would be a problem.

Fact is, with any govt regulation, it’s not whether you’ve done something wrong…it’s whether they decide to frick with you.
Posted by iosman987
Member since Feb 2020
46 posts
Posted on 8/21/26 at 3:23 pm to
Not sure if you already found someone since it's been a few months, but if you're looking into STR vs LTR, a regular CPA might be enough if you get the right studies done on the property.

The big tax savings usually come from cost segregation. It basically front-loads your depreciation so you get massive write-offs in the first few years.

I sent my property details to R.E. Cost Seg and they gave me the exact breakdown. I just handed that report to my regular CPA, and it lowered my taxable income big time. Might be worth checking them out to see what kind of deductions you can pull.
This post was edited on 8/25/26 at 8:31 am
Posted by Bobandus
Member since Aug 2018
210 posts
Posted on 8/22/26 at 8:13 am to
I've been trying to figure out how to do the same. Would love to know how i can stop getting screwed as a w2 earner.

If i get a side gig as an independent contractor working a day a month or so, could i somehow use that to my advantage significantly?
Posted by CharlesUFarley
Daphne, AL
Member since Jan 2022
1186 posts
Posted on 8/23/26 at 5:08 pm to
Have you ever considered raising emus?
Posted by LSUFanHouston
NOLA
Member since Jul 2009
41733 posts
Posted on 8/23/26 at 9:40 pm to
quote:

If i get a side gig as an independent contractor working a day a month or so, could i somehow use that to my advantage significantly?


Define significantly

Pigs get fat, hogs get slaughtered

And showing a loss 4 yrs out of 5 can invite an audit. Maybe.
Posted by LSUFanHouston
NOLA
Member since Jul 2009
41733 posts
Posted on 8/23/26 at 9:41 pm to
quote:

100 hours is easy to hit


Yes - for self managed properties

quote:

Don’t know why this is even a discussion


The “more hours than anyone else” rule is what causes the discussion
Posted by makersmark1
earth
Member since Oct 2011
21635 posts
Posted on 8/24/26 at 5:32 am to
Learing centers are depending on you paying more taxes.

How can all the necessary hospice funds be given IF you try to dodge paying your fair share?

There may be a delay in gender reassignment surgery because of people like you.

The weather will never be better unless you pay more taxes.

Why are you a misogynistic racist?
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