It can be easy.
I had a tiller pilot on my Cal 27-T/2 and could fly my spinaker solo up to about 10 knots of wind (that is, until I shredded the antique elephant-butt kite). About that point it can become pretty dicey and that is enough wind for cruising down wind anyway. An asymetrical cruising chute is even easier to fly shorthanded as you don't need to mess with a pole and the control lines for that.I don't believe you can learn to set, douse and fly a symetrical or radial chute very easily from reading instructions. There are a lot of little tricks to make things go well and several 'don'ts' that you would wish to avoid. If you have a radial chute, I'd suggest you hook up with a spinaker class skipper for some of the Saturday races with the Pamlico Sailing Club. Next race is #3 on Saturday April 3rd. Link to the club is below.Racing requires a crew of three, in my opinion, to get the most out a spinaker on anything over about 25 feet. Cruising is far less demanding and on a boat under about 30 feet, it can be done solo if skilled and with two if you have the basics down pat. You really don't need to trim it much then, just sail under it. Head upwind a little to set and douse which allows the main to partially blanket it and simplify the process. Have all control lines stopped so that you won't lose them if they get away from you (and they will now and then). Yet, your stopper knots have to be instantly releasable if you goof up and start 'shrimping' (dragging the spinaker filled with water).I'll be glad to meet with you some time, check out your rig and give a few pointers or give an on the water lesson if time permits. Look up www.statewidetitle.com and call me at the Greenville office if you would like to do so.