Re: Help what sail to raise 1st?
On a sloop, main first, then jib. Furling, it's jib first, then main. Others have outlined the reasons. Anyone who tells you different is telling you wrong. You only have to be at the mast with the genoa slapping you upside the head because you went jib first to realize why.
Learning on a small boat is fine, just remember, the bigger boat is...bigger. Bigger loads, more momentum - the basics apply, but may have to be adapted to the boat you are on.
In strong winds, it's possible (and often smarter) to furl the jib by hiding it behind the main so that there is no wind in it. Then turn into the wind to furl the main.
CYA Basic Cruising Instructor
Delivery and Charter Captain