A year after I wrote this post I got a PM from someone looking for some help with QuickBooks and I realized that I had chnaged my opinion about 180 degrees and should propably close the loop here. So, what happened in the last 12 months?
QB (or a similar software) is definitley the way to go, however I would not recommend today anyone to take the same approach I did and doing it by yourself. I have spent a lot of time, energy and money (online coaching on QB) to get everything set up. I got it to the point where I had all my properties set up and was able to properly record all income and expenses. However, there were still quite some wholes in books. For example I did not upload all my credit card statements and bank account statements to reconcile with my records and actual spendings. Most of materials are paid with credit cards and they need to be tied to receipts line by line and also when paid at the end of the month tied to the correct line in my bank accounts.
So mid year I had a meeting with my CPA to determine what was still missing. To be perfectly honest I felt overwhelmed and started to realize that I would never get the books to where I wanted them to be while holding down a job that requires global travelling and running rehabs on the side. Quite frankly, even with out those things - I am just not a natural as an accountant. My CPA said he'd be able to get everything caught up at the end of the year, but I've been through this last year and that was very costly and time consuming (CPA hours are way more expensive than book keeping hours). So I was driving home feeling a little defeated..
I started to realize that me doing the books was the equivalent of me doing a contractors job. And while I get some satisfaction out of laying tile, let me tell you there are a few things that I dread more than book keeping! So it became pretty obvious I needed a book keeper. Turned out I am not the only one comeing to that realization (most small business owners suck in accounting) and there are plenty of services offered. After a quick google search I interviewed a few in close proximity to my home and made an appointment with the first one that told me they did work for a few appartment building owners.
I did not realize at the time that this was my best Christmas present this year. It took a huge load of my shoulders and I could finally focus the few hours I have at night on what really matters (finding the next deal, managing my rehabs and a little bit of property management). While they charge me about $30 an hour for basic book keeping the person doing the work is probably four times faster as I was. They quickly closed the gaps in my book and got everything to match and reconclie with my accounts. The best thing is they are working with the same QB file that I have on my laptop, so I have the data on my machine any time I need it.
Now I am able to create a complete and verified P&L (profit and loss) statement, a balance sheet and a cahs flow statement for any given period of time with a few clicks. This is a huge help for me to manage my business, makes taxes easy and is a huge benefit when working with lenders.
Bottom line: if I would do it all over again, I would hire a book keeper right when I bought my first rental property.