@Cary Ferguson Jr points that out in his excellent post. 

Yes, excellent idea!

@Cassidy BurnsIf you have a couple properties(1-4 properties) - it isint too difficult to do your own bookkeeping inside excel or google sheets.You should export the monthly statements to excel and be able to properly categorize the expenses(utilities, real estate taxes, mortgage interest etc).However, once you get above 4 properties - you should look to having the bookkeeping outsourced so you can focus on tasks that bring in more money to the business(looking at deals, making offers etc).You can certainly hire a Virtual assistant to do the task for you.

Matthew, Excellent and thorough post! 

It just stinks because I have excellent credit and my deals are good ones suitable for bank financing.  

Main floor and bedrooms only need new paint, all floors on main and 2nd floor are solid hard wood and in excellent condition.  

-if you can get references of roofs that he’s done that are a couple years old (talk to those customers and you can get an idea as to how they have held up for a couple seasons)- See if he can throw in a manufacturers warranty GAF has an excellent warranty program that might be valuable if you have any issues down the road

Ideally having the servicing notes is an excellent research tool.

Excel is no longer scalable for us and we are looking for a platform that will allow us to put in forecasts for the properties and ideally pull data in from an accounting system to report.  

He'd be an excellent person to chat with.