The main reason I dont like pruning so much is its just me, so its slow, and I get real anal about it so its even worse, I never make much at it.
The "trick" is to bid it so you can do it well and on time. If it is one you can do on a cycle, then set it up so that one or two trees are done on any given visit. You do not have to get it all done that day.
Maybe you can concentrate on "hazard deadwood" over high use areas and tip thinning to reduce leverage loads.
One problem with getting into high income areas is that some think that those people will have a huge amount of disposable income. In reality that is a small percentage of the population, like you and me those people live within their means, or are just as much in debt.
Proposing a cycle that is manageable will help you maintain the relationship.
Work in some high-vis work with the low vis, this way you don't get all that they can see done at once, causing them to think it is done.
Quite often I'll propose not doing entire trees on a given visit, because it will be easier to transfer from one section of tree A to get something in tree B. Then go from tree A to tree C on the next visit.
When I worked for this other guy there used to be three or four good guys aloft at a time, thats how you do it if ya can. For me just having another guy doing close to as much as me and doing it right would be an amazing help.
Tag team's are nice, when everyone is on the same page. Find someone who is better then you to work with you on a bigger winter project. This will help you push yourself.
On the other hand it can generate so much more debris, that you get buried. I had a client 2 hours north of me. He chose to not use me any more, because it would take him 3 days to catch up on the clean-up.
Lastly, what will you have to pass on if you are a removal tech? I heard it put very well on the myXM the other day, some people can spend 10 years building themselves a great job, while another guy can start the same thing and build a business he can retire from.
If you have a client base that you can sell to as you turn the company over to whomever buys it, you will be better off as you phase out.