What return on ad spend handicaps are typical for new user acquisition in big box retail environments?

The only AdWords keywords that will perform well on search are ones that directly describe your product, e.g. "document syncing." To target a segment like legal professionals, use AdWords' Contextual Targeting Tool to build ad groups to target websites that your target market would visit, e.g. anything related to law.

I have worked with a client with a similar issue. Their competitor was bidding on the brand name of my client. You will have to donate some Adwords spent and create “branded campaign” where you focus on bidding on your client’s business name. Your client should have a high quality score for their brand keywords since their website should but an authority on the brand name. As far as stopping a competitor from bidding on the name the most you can do is send a cease and desist letter and I would only recommend this if the brand name has a registered trademark.

Make sure you've setup advanced analytics. You'll get a better picture of which conversions were direct, and which ones were assisted by another channel. Use tags and make sure your urls include all the detailed parameters - note that savvy users might truncate that link, so use a link shortener (like bit.ly) to mask it.

I've done a lot of complex analytics installations, usually cross-domain and including AdWords and manual tagging with conversion tracking of ecommerce transactions. The gclid by default will override the manual UTM values in Analytics so that is what you are looking for. If you are just grabbing the manual tags from the URL for your own purpose, this should be OK. However, if you at some point want to import conversions (say) connected to your manual tag, then you would want to enable UTM overriding the gclid: https://support.google.com/analytics/answer/1033981?hl=en. Do you have AdWords and Analytics accounts linked? Where and how are you tracking commerce conversions, if you are? Do you feel you are getting the insights you need from your current custom reporting? Let me know if I can help with a call about those or further optimization of your analytics capture. Best - Michael

Depending upon what aspect of AdWords you want to automate, you can look at various tools. As Megumi suggested, Marin is a good option for bid management. You can have a look at Optmyzr (optmyzr.com) to automate account management activities. Cyfe is another option to automate reporting and building dashboards.