Main Sail

Yes it is a challenging task. After a period we developed a process which is -

Put the boom way out to one side and pull it down with the vang as far as possible. The end of the boom will be out board and at a reasonable height so you can reach the zipper to start the closing. Pull the sides of the sail bag out as you go and pull the zip forward a meter at a time until you are about half way along the boom. We have a rope about 10 meters long with a monkey's fist at one end. We tie the other end to the zip and throw the monkey's fist between the lazy jacks and past the mast. I then climb up on the mast steps (we had and extra two steps put on the mast so I am above the sail bag) and then I pull on the rope attached to the zip which generally comes easily and fully closes the sail bag. I leave the line attached to the zip and coil it up in the sail stack. Then we let the vang off and raise the boom and center it.  When we go to use the sail I climb up the mast steps , pull out the "throwing line" and throw it to the aft between the lazy jack. Whilst I hold the sail bag my wife pulls the line and the zip easily travels to the aft of the boom. Undo the line and you are ready to raise the sail. It sounds more challenging than it is. Using this method we don't need to put the bimini or dodger down.  Give it a try. 

I will try in my boat and will let you know how it was 

I had full battens, lazy jacks and a huge main for 25 years before getting my roller furling boom.  As I got older it became less of an "accomplishment" and more like unnecessary work.   On the sixth boat (14'-->33'--->40'--->45'--->49'--->575) I decided to splurge :-).   You don't sacrifice any performance from what I've seen with the boom option.  The Hanse option was expensive.   I did it post-delivery for about half the price.

I found that it was all about boom height.    Some boats (like my Island Packet 45) were easy.  Others not so much.    This is why I always liked to sail on the boat before buying it so you can see how the furling mast (usually jammed while rolling out) or stack pack (what Hanse does by default) are like.  

FWIW

The 14' was an O'Day Javelin.   My wife brought it to the marriage.   My previous experience was on Sunfish only.      The Island Packet 45 and the Hylas 49 were great boats.   We built both of them and visited the factory when they were being built.    Big, rough weather designs such that I was never worried about the boat.  Maybe my skills, but not the boat....    

The Hanse is a much more modern design, with a lot more room, and much better sailing performance.  Both the IP45 and the Hylas were cutter rigged and needed a lot of sail to move even in a stiff breeze.  Both were set up for the ICW with shorter masts and that certainly isn't possible with the 575.     The IP45 and the Hanse are probably equal build quality, but the Hylas was like a piece of jewelry.  Queen Long in Taiwan makes outstanding boats and their service is the standard as far as I'm concerned.

I'm not doing offshore anymore, so this is just for coastal cruising and the comfort of my wife when we do extended stays on the boat.