There are 2 specific areas I let folks know about before securing Wordpress development help:

1) Plugins: Discuss with the developer their thoughts on plugins and how they should be implemented. Does the developer want to write their own? If so, discuss ownership and existing support. Leverage existing plugins? DIscuss conflicts of support among changes developer made vs. plugins.

2) Hosting: Non-technical people sometimes don't understand the effects hosting can have on a small business website. I suggest to them to ask the developer for their thoughts, especially if the developer is doing the hosting.

Wordpress is a great platform for small businesses.