I highly recommend using a jib roller furler system if only for the fact that adds and extra 20-30 minutes of sailing time to every to every, it makes getting underway, and then packing up on return, much more convenient.
It can be cumbersome without a specific folding technique. If you're on a mooring... I agree that a furling system is way, way easier. However, at some point you must remove the sail so it's important to know how to get it folded and packed away. If you're at a slip... it's just a matter of pulling the sail off and stretching it out on the dock. Fold from the bottom, pulling each section down accordian style until the head, clew and tack are all on the same side. Then, from the clew end... start rolling the sail, loosely, towards the tack. Insert the bundle into the bag with the three corners on top. When you remover to install... lay the bundle on deck... the tack will be the outermost corner and you can simply clip it on first, then unroll the sail on the foredeck towards the mast... if you're using hanks.... you can straddle the sail and clip them on before attaching the halyard... then tie on the sheets with bowlines... separate sheets make this much easier than one long continuous sheet with a cowhitch. A single sheet works well with dinghy sized boats.... but not so well with boats over 20 feet. (just my opinion, don't get riled up). Besides, leaving the sheet attached and stored in the bag with the sail creates all kinds of problems for the sail and makes the whole package twice as cumbersome. Separate sheets can be run ahead of time... or left in place if you're just changing sails. Can't do that it the sheet is already attached. Okay... enough... you get the idea. Nothing wrong with furling.... but neither should you let the hanked on system cramp your sailing pleasure.I don't see how a large, crisp head sail is all that easy to get into a bag. Especially when single handing. It was a PITA just bending it on once. The furler life for me
When I bought the boat my main intentions were to get something that was ready to sail and allowed me to get out on the water without having to spend a lot of time fixing and repairing. Now that I know more of what I appreciate on a boat, like, don't like, etc. I found that I'm leaning towards eventually getting something in the 30' range with a wider beam. I just want the extra space but don't want a massive boat. 35' would be the max I would want to go. I'm weighing out the cost of all the upgrades I would do vs just buying a boat that has those upgrades already in place.I enjoyed the process of my hank jibs on my O'Day 25. I had 3 head sails, a 115, a 150, and a drifter. Changing sails was easy and fun, even worked on a system while racing underway to do it. I even bought a new 115 with reef points and kept the hank on system. Now with my 310 it came with a 135 on a roller. It is supper cool and easy to unroll the sail and rolling up is fast and convenient. But I'm learning it is more challenging rigging a code 0 and makes it more complex.
Your pic shows a yankee bag which I always thought was a nice compromise for hank sail handling. What is your intention with the boat, how long do you plan to keep it? Any thinking of maybe upgrade? I loved my O'Day 25 but after a few seasons I figured out what we needed and saved upgrade money for a new boat.