I just purchased my first rental. My goal is to purchase 20 over the next three years. What is the best way to keep track of income/expenses? Is there a bookkeeping program that is simple and accurate or should I find a bookkeeping service to handle this for me?
At this level you want to keep it simple and easy. Try quickbooks for business. There are a zillion others for Rental properties. I know a company that manages over 100 units on Quickbooks. Not a great idea but it works. Start simple and get it done!
Quicken is overkill for the first 20 properties. Quick book is more than overkill for the first 20.
quicken home and business will get it done for you and keep you organized and has rental reporting features like cashflow reports and schedule-E end of year reports. You download your bank/ credit card transactions on a weekly basis into quicken and then tag transactions by property and expense/ income type from a pre-populated drop-down. You can tag/categorize once a month to keep organized so at year-end all you need to do is turn in an exported schedule E report to your CPA. quickbooks requires alot more training and is not intuitive to setup for rentals and doesnt have the functionality built out of the box like quicken. It's also the lowest cost bookkeeping software I've found that's an alternative to cloud-based Software.
rental hero is awesome. $119 for the year and its really easy to use.
QuickBooks all the way someone starting out and growing to 1000's of property. Right as you grow look into a property management software for automation and using QuickBooks for accounting. It is easy to segregate and not do any double entry.
Have one client with over 5000 units who AppFolio for tenant management and QuickBooks Online for accounting.