This might be overkill and is all based on your risk preferences.

Should I be wearing a full suit or is that overkill?

I use Access to manage my list but it is overkill for a smaller list.If you are using Excel or other spreadsheet, create a new field to flag records to exclude from your list and use the help button to find tutorials how to filter out records you don't want to mail.

Obviously, that would be overkill for putting in $5k, but at $100k that story changes.  

(it was overkill) Now that I can't see the houses because I am not there, I do more deals!

Sugar is a good one: http://www.sugarcrm.com/crm/products/crm-products.htmlAlthough, from the sound of your request, it could very well be overkill for your needs.

I know this may be a little bit of a over kill but the second time around my goal was not to barely pass with a 76, but shoot for the 100.

(overkill I know).

Depending on the demographics of your rental this may be difficult to implement (especially on short notice - I now require it for new tenants).We're both in that sweet spot where a part/full time employee is overkill, but the cost of a PM seems excessive when most things can be done remotely these days.  

This might be overkill, however you did ask.Remember that you are asking specific questions on a national forum.