It sounds like you have some good ideas of what you are looking for. Catering is nice especially if you aren’t used to fluctuating income but its going to be off and on and seasonal at least in the beginning. Farmers markets are a good way to get a small steady fan base quickly. But I would recommend only doing weekday markets, as there is way more money to be made at festivals and events on the weekends. Average weekday farmers market in Seattle area sees $300-500 in about 4-6hrs in sales. However on the weekend market you may tap out at $1200 for the day. A Festival on the other hand can range $1500 on the low side to $4000-$8000 per day depending on size and level of competition. That’s not to mention County & State Fairs. There you may be setup for 3 days or more, sometimes up to 3 or 4 weeks. But your local Restaurant Association will usually hold trade shows and lunches to discuss the more catering side of things they are well worth attending.
These links may help you.
As far as specialty cups go you may want to wait till you have a better handle on portion sizing there is nothing worse than buying 1000 of anything only to realize that its costing you more that your making to serve on that scale. Besides custom cups/bowls will cost 3-6x more that standard ones. But Check your local Restaurant Depot, Business Costso or Cash & Carry suppliers then search for custom printing. Also another thing to keep in mind is that some cities, organizations and such, require 100% compostable products you may have 3000 logo cups but if you can’t use them they don’t do you any good.
Wrapping is a tough call to make. You definitely want to wait until you have finished that fabrication portion of your build but the last thing you want is to do it too soon and have it damaged because of moving equipment around or the like. We are doing the wrapping after we pass inspection with our local Labor & Industries so incase we have to 11th hour redo something we aren’t having to waist time and money to have it redone.
Hope that helps,