When I was providing website and blog hosting services (I still do but not as much) I had an automated billing system.
The system, called WHMCS, provided automated billing, support, setup, etc. It’s the full package for any hosting provider!
When I decided to fade away from the hosting services, I also decided that I could do the invoicing manually and not pay the measly $15.95 per month for WHMCS. That was one of the WORST decisions I had made in a long time!
After cancelling my WHMCS account/license, I had to manually enter in appointments into my Outlook calendar so that each month I knew when to create and send out invoices, and when to process those invoices. It actually took quite a while to achieve this because some of my hosting clients were paying monthly and other were paying yearly. This doesn’t take into consideration that when I needed to write up a quote for a prospective client it took me longer as well.
So after manually invoicing my clients each month for about a year it became too tedious and took away quite a bit of time from my work. THEN, Verizon (I have FIOS) decided to beef up their security for sending and receiving emails, whether it was through their servers or not (I have my own servers and domains, etc.). This wasn’t an issue with sending and receiving email through Outlook, but the invoicing software I purchased to replace WHMCS did not allow for configuring of the SSL email parameters and I had to create the invoice, then print it to a PDF file, and then manually email it through Outlook. Obviously this was not an ideal solution, but it worked.
I contacted the company who wrote the replacement software I was using (Avanquest) and they weren’t much help, I don’t even think they knew what I was talking about. Their software is good, usable and inexpensive, but the tech support leaves a little bit to be desired for the most part (They have resolved other issues rather quickly). This is a challenge because quite a few ISPs are now securing their email services to prevent spamming, hacking, phishing, etc. and more and more of them are joining the fight every day. I applaud the ISPs for their efforts, but the software companies need to catch up.
At any rate, the only logical solution to this conundrum was to return to an automated system. I chose to go back to WHMCS because it is such a fantastic program! It contains a client area, support desk system, automated billing, automated hosting account setup, quote generation and quite a bit more! It was a mistake for me to ever leave to save a lousy $15.95 per month (You can purchase it outright as well for a couple hundred bucks)! Ok … so we all have moronic moments … this was one of mine 
It took me a day or so to get the WHMCS installed and configured with all of my products and client’s information but now that it’s set up, I’m done! Now everything is automated again for me, except quoting – that’s manual. But once a quote is accepted by a prospective client, one click of a button in WHMCS converts it to an invoice and then will process their credit card automatically at the specified time. I use WHMCS for EVERYTHING related to my accounting for ALL of my clients; hosting, web design; technical writing … everything!
After going through this scenario, I can confidently state that sometimes when you try to make things better and save a few bucks, you end up screwing yourself up worse than if you just left well enough alone. Don’t put yourself into this situation and take away from your productivity; automate your invoicing and be done with it. You’ll pat yourself on the back every time you see another invoice go out and get paid without having to touch a single thing!
