Vacation Rental Tax Tips for Tax Professionals

Drake Software Blog Team - June 03, 2025

As summer travel heats up, many taxpayers turn their second homes into short-term rentals. While the extra income can be lucrative, it also introduces a complex mix of tax rules that require attention from seasoned tax professionals. If your clients own or are considering listing a vacation rental, here are key tax tips to keep in mind for the coming tax season and beyond.…

Customer Spotlight: Dorothy M Reep CPA PA

Ryan Norton - December 11, 2017

Dorothy “Dot” Reep of Dorothy M Reep CPA PA sits behind a desk decorated with postcards and affirmations neatly arranged beneath a glass table top cover, business cards from clients stacked in rows, and—most importantly—photographs of her grandchild and great grandchild, keeping her attentive gaze trained on the Drake Software interview team.…

Gary Boykin, EA: Tax Prep is a Family Tradition

Ryan Norton - February 01, 2017

While growing up in Jacksonville, North Carolina, Gary Boykin was first introduced to tax preparation at the age of four: “I remember running around the dining room where my dad was working on a…

Jim Bourke, CPA, CITP, CFF, CGMA: A Passion for Technology and Tax

Ryan Norton - October 11, 2016

Bootstrapping seems an appropriate way to describe Jim Bourke. Some may immediately recognize him as a tax-industry luminary whose dedication to spotlighting and adopting efficiency technologies has led to industry-wide adoption of workflow and organization solutions.…

Terry Durkin, EA, MBA: Two Generations of EAs; Two Generations of Drake

Ryan Norton - July 01, 2015

“You’ll know what to do.” Terry and her mother had always been close. After Barbara Durkin was diagnosed with lung cancer in 2003, Terry decided to come home and help with her mother’s tax practice. When talking about their relationship, Terry reminisces, “I can’t describe my mother in just one word: She was my role model, my friend, my mentor, and so much more. She was influential in every part of my life.”…

Two Styles; One Successful Practice

admin taxing_subjects - September 30, 2014

Facing Challenges - Creating SolutionsThe Challenge: Melding two management styles and different levels of experience into a single, client-focused tax practice.The Solution: Recognizing that clients…

Tax Practice Success and “The Five Ps”

admin taxing_subjects - June 30, 2014

[caption id="attachment_5231" align="alignleft" width="136"] Tax Practice Success[/caption]The Challenge: Sustaining growth and profitability in the mature markets for tax preparation services.The…

Larry Kessler: It’s Not What You Make...

admin taxing_subjects - April 01, 2014

It’s What You Keep Larry Kessler Financial Services is an example of how to create an accounting firm built on friendships, trust, and fair dealings. “I don’t advertise,” he says. “I focus on giving…

Journey to Success

admin taxing_subjects - December 31, 2013

A tax professional recently elected mayor of his town shares the story of his journey to success.Pat DeBlasio, a tax professional and political leader, was recently elected mayor of Bridgeville,…

Loyalty Matters

admin taxing_subjects - November 04, 2013

Loyalty Matters: Edward GonzalezEdward Gonzalez is a successful business owner, a dedicated professional, and a devoted husband and father. He is honest, outgoing, friendly, and has strong moral…