You're asking three questions:

1. How to hire an outsourcer to generate leads: If you want someone to do your cold calls for you, you need to be very specific as to the script you provide, and the actions taken before, during and after the call to record and maintain records of all communication. That will probably involve software you'll need to train your VA on. The script depends on the outcome you want from each call. That brings us to the second question.

2. How to approach your market: You'll need at least one call script for each market, and you'll need a clear desired outcome for every one of those markets. A conversion from one of those markets is not going to be the same as a conversion from another, and the average value of a conversion from each market will vary, too. This is something you'll learn as you go, so don't set and forget.

3. Whether your market is the right market: You don't have to narrow it down, but if you feel the need to call so many different types of people about your services, it means you don't feel confident you could make enough money from just one or two. That's an internal issue that needs addressing at some point.

Another tip: make some calls yourself, first. Live what your contractor will be living, hear the objections, the tones of voice. After the contractor starts, listen to some of the calls, and keep making some of those calls regularly. It will help you adjust your script more quickly, and decide more quickly whether your contractor needs to further training or an upgrade.