Skip to content
×
Pro Members Get
Full Access!
Get off the sidelines and take action in real estate investing with BiggerPockets Pro. Our comprehensive suite of tools and resources minimize mistakes, support informed decisions, and propel you to success.
Advanced networking features
Market and Deal Finder tools
Property analysis calculators
Landlord Command Center
ANNUAL Save 54%
$32.50 /mo
$390 billed annualy
MONTHLY
$69 /mo
billed monthly
7 day free trial. Cancel anytime
×
Try Pro Features for Free
Start your 7 day free trial. Pick markets, find deals, analyze and manage properties.
All Forum Categories
All Forum Categories
Followed Discussions
Followed Categories
Followed People
Followed Locations
Market News & Data
General Info
Real Estate Strategies
Landlording & Rental Properties
Real Estate Professionals
Financial, Tax, & Legal
Real Estate Classifieds
Reviews & Feedback

All Forum Posts by: Greg O'Brien

Greg O'Brien has started 2 posts and replied 381 times.

Post: Question on Short Term Rental Loophole

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@Jay Yoo The Regs have Seven tests. 100 AND more than anyone else is a test.

Post: Advice for transforming our high-end primary residence to a STR (abroad)

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@Liz Caskey unfortunately you cannot use Accelerated/Bonus depreciation on Foreign assets.

Post: Offshore trust anonymity

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@David Pimenov no. Lots of scams out there we’ve see . You are taxed on your worldwide income.

Post: Alternatives to Wealthability for tax planning

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@Tony Sorensen Tom is extremely smart and has excellent content. There are many threads on BP with reviews and experiences.

Like others said, look around for tax strategy focused firms and talk to a few that may better fit your needs!

Post: Guidelines for what to expect to pay a CPA for first year LLC taxes

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@Corinna Woodcock this was a Partnership? If so that is pretty standard for a one off fixed fee.

Nothing is apples to apples though when it comes to scope and pricing. Every CPA bills differently and includes different items. Some bill fixed fee, some hourly, some have subscription models.

What did this include? Was all bookkeeping reconciled etc?

Post: Tax Planning Ahead of Rental Portfolio

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@Connor Benn Id agree be proactive. Education and Implementation is the name of the game.

Post: The STR loophole

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@Jon Martin the rules have been around since 1986! The “loophole” is just a specific subset of Regulations for transient rentals, which have been around forever, but of course became more popular recently.

The IRS cannot change the law so it will likely not change until a major tax package gets passed but even then, this isn’t a blip on the radar of tax policy.

Post: The STR loophole

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@Andrew Caldieraro read this! https://www.biggerpockets.com/forums/530/topics/1056436-clearing-up-confusion-on-tax-treatment-of-short-term-rentals

Post: Clearing Up Confusion on Tax Treatment of Short Term Rentals

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

@Jon Fletcher no, there’s no hard and fast rule. Technically, the IRS could pursue the Substance over Form doctine if they believed this was all done for tax avoidance in pre planned steps.

Post: Can I use accelerated depreciation on 1 property to offset capital gains on another

Greg O'Brien
Posted
  • Accountant
  • Boston, MA
  • Posts 386
  • Votes 335

Basit is correct. So long as both are passive they’ll net.