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It is very important; security, backup, maintenance etc...
The problem is there are two kinds of customers, cheap and cautious. Cheap only wants to pay $12 a month.. and does not understand or want to understand that not having maintenance is a bad idea. The cautious ones pay anywhere from $50 to $500 for a managed WordPress web hoster for their site. Why would they trust you? So what you are saying is that you want to educate the first group to understand they need help or get the second group to trust you more. Both are very hard sales... What I do with both these groups is sell them management included in the price of the full package. I don't know if your doing something else here. Another interesting Idea that I had, but don't have time, if your really good with fixing WP, let them break it and then charge them to fix it... Might be an easier sell.
As long as you pay your taxes, I don't think any government cares. However you are just causing yourself more reporting issues and problems. You have to file corporate paperwork in both states, is it worth the paperwork. Easier to get either a new corp, or a new register agent in location where corp is. Anyway the bigger problem I see is; how do your customers see it, are you losing business because of it, are they thinking your hiding something... I see this all the time with people selling in Florida, but have a Nevada Corp. People don't trust them as much, And isn't sales all about trust.
Establish a sales funnel.... Use cheaper / less experienced people to qualify and make appointments whether personal or virtual. Use more experienced people to have a conversation and/or the final close. Most sales are a three step process, especially in a higher value item. Don't rush the close, establish the value. Apart from this basic idea, everything has to be custom tailored to your particular needs. Let me know if you need further help developing this.