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starting simple is always a good idea ... composite decks get pressure washed, i did about 15-20 of them this season (usually $200-300), always nice cause the railings are nice & easy and they'll be the first customers I call in 2012 ... & not to make your head spin, but you can soft wash vinyl by downstreaming (hit search button, ton of info) through a pressure washer. it's faster & in my opinion easier, than using your roof pump & you'll use less SH ... you might decide to hold off on the pressure washer, but I'd say 9 out of 10 roof cleaners use one in addition to their roof pump

also, don't worry about bouncing around like a pinball. as you mentioned start off slow and let things fall into place. you'll learn more in your first week on the job then you will all winter reading through this forum. if you're interested i have an extra 5850 "pump in the box" kit from pressure tek. i would sell you one, complete with hose, nozzles, etc if you're interested. the only thing you'll need is a 55 gallon drum (free) and a battery ($75). you can use it, see how you like it, and then make a decision on which way you want to go. you might want to use it for the season, or if you decide to upgrade, you can use it as a backup. the nice thing about that, aside from not having a hose reel, is that it's portable & you can test it out in your pickup, as well as your trailer, and then make a decision on where you want to mount it.

i really can't offer an opinion as far as what you should choose, just can share my own personal preference which is based on a set of circumstances that may be entirely different from yours.

how often are your remodeling & siding trailers used? do your employees perform the labor or do you? how much time do you plan to dedicate to roof cleaning? how often are both pickup trucks used and do you use the beds to transfer anything. also, will you be getting your SH delivered or will you be driving to pick it up, in which case you might need a pickup truck to transport? if demand requires the purchase of a pressure washer, where would you mount that?

how about storage? i prefer to keep my trailer indoors overnight ... point being, there are a lot of things to consider that only you can answer. if i was confused about which way to go, which you seem to be, i'd want something simple & mobile, so that i don't mount an air compressor and a hose reel to my pickup truck only to decide a week later that i should've put it on the trailer.

Sounds like youre on the right track. I would say not to use the van. SH eats EVERYTHING. Also, the fumes would be tough. Be sure to use your PPE ie respirator ( just a painter style with carbon filter) and Gloves. My research says don't use Dawn as a surfactant. It releases Flourocarbons when mixed with Bleach. Says so on the label on the back. Use a good surfactant like ammonyx Lo or Mo, Talon or Green Wash. You shoould be able to find references and answers to the questions this will raise. Welcome. If I can help my number is listed. Call anytime.