Each month, the Property Manager Q&A Blog will pose questions for a group of property managers to address. The list of PM participants range from around the US with inventory large and small to ensure all perspectives are reflected and captured.


Should you have questions you want to ask, feel free to post it in the comments section.



How did you become or get into the property manager business? And do you think it is easier or more difficult for young people to come in the way you did?


Steve Milo: It was by accident. I originally started managing my own vacation rentals due to the inability to find a competent property manager in the area of Venice, Florida. My background is technology, and I built a website and spent a lot of time on search engine optimization. I was having so much success with filling rental demand that I was approached by friends to manage their properties. Soon, I had friends of friends approaching me. I left my full time job in late 2005 to devote my full time effort to Vacation Rental Pros. In less than 6 years, I now manage 435 properties. In my opinion, the property management industry is entering a stage of a "digital divide." Those companies with strong technology platforms and internet marketing will significantly outperform companies without technology skills. If you are skilled in the use of technology, you will find a niche, and you will have a strong chance to succeed. If you are weak with technology, you will have a very difficult time.


Tim Cafferty: I was born into it. My father was one of the original REALTORS in this area, and I started working around the business when I was 7-years-old. I had aspirations of doing something else as I grew older, but the draw was too strong, and I’ve been doing it now for nearly 30 years. I think the business is easily accessible to career minded young people. There are lots of opportunities for a serious-minded, young person who has good customer service skills and is willing to work hard. Call me I’ve always got opportunities!



How have bookings trended in your market over the past two years?  Have companies in your area dropped prices or demonstrated any other methods to keep demand up—and what do you think about these trends?



Tim Cafferty: Bookings have trended upward in the  last two years relative to volume and income per house over the last two  years, after a few years of decreasing demand and pricing. Trends were  headed downward for several years in this area until last year when they  started a slight turn around. Guests have become very savvy over the  last few years about comparing prices and knowing what the value of a  particular house for a particular week is mainly because of the ease of  comparison with the Internet. For this reason, proper pricing is  critical for our properties. We have focused on this and our occupancy  rates in this area have been very good as a result. In this area our  main feeder market is the Washington DC area which has seen government  supported job growth and a good overall economy. This has no doubt  played a part in our positive trends and good fortune.


Steve Milo: We are seeing a shorter window for bookings and more of a drive-in market vs. a fly-in market due to the recession and to the cost of air. There has also been a remarkable trend to pay with credit cards vs. checks and consumer reviews are becoming more and more important. Most of all, we are seeing almost every guest use our website for research and in many cases direct bookings. We have adapted to these changes by improving our website, improving our booking engine and creating an easier to understand search engine and calendar function. We have embraced consumer reviews and now have over 6,000 reviews on our site.  We have improved all of our photos and have high resolution images. Our efforts to improve our website have resulted in higher occupancy and rate increases for most of our properties.



About Steve Milo

Steve Milo bought his first vacation home in Florida in 2002, and shortly after, began purchasing additional vacation homes in Florida and managing vacation homes in St Augustine Beach, Venice Florida and Palm Coast Florida. In 2005 year, Steve founded Vacation Rental Pros Property Management and manages more than 400 vacation rentals in Florida. You can find more information at: VacationRentalPros.com.


About Tim Cafferty

Tim has been in the property management business for nearly 30 years and runs Outer Banks Blue Realty Services, a  family owned and operated vacation rental management, property  management, and real estate services company operated in Kitty Hawk,  NC. founded in June, 2005.