This is the kind of info I wish you'd provided sooner. It seems to me that your mowers are kind of redundant and all small....a 21, a 22, a 32, a 33 and a 44. Since you already have a 33, call that your gate machine...probably won't use it much so it should do for now even though it's a Craftsman, and you have a 22 that you could use in gated areas if that failed on you. So skip the new 32 and 44, because 44 isn't much bigger. I'd say just add a 48 or 52 inch hydro walk behind with a sulky and call that your primary mower. I like a 48 because you can always load it into the truck and there seem to be a lot of landscaping features only 4 feet apart....just a pretty versatile machine that you can use on anything from a 5,000 square foot to a 1 or 2 acre yard.
I'd step up in the blower category if you plan to do cleanups at all, and if you're maintaining lawns that's kind of a given. If you're sold on Echo, the 770 is a nice machine...almost bought one but found one I liked a little better. The bigger blowers really save a lot of time and if you're solo it's all about efficiency. An extra $200 or so spent now will pay for itself quickly and then over and over as time goes on.
Honda makes nice mowers, but do you really need one now?
I think you could make a decent go of it just adding a 48 inch hydro mower and a big blower. As you add accounts and need to increase your efficiency or your Crapsman stuff breaks down you could buy the pro stuff as you go. A 7 x 12 trailer is a good size to start with and for many to stick with (what I've used for 11 years but I have a dump trailer too). The truck should do as well, even though it's the wrong brand, lol.