My first boat was a Hobie 16. I sailed it solo most of the time and it was a decent little craft but not showing it's age well.

I quickly moved up to a G-Cat 5.7M (18'9") which I primarily solo. This beast weighs in the same as a TheMightyHobie18 but is harder to drag due to it's Deep-V hulls. If you solo, you need to have Cat-Trax. There is simply no getting around it unless you never have to move your boat around on the beach.

As far as the mast-stepping goes. Figure it as a good workout I use an extra line tied to the jib halyard, going through the bridle ring, and back to the base of the mast. I heave the mast up, pull the slack out of that line and cleat it off to the base of the mast. Then go forwards and attach the forestay. I've been doing this since I was a 5'9" 140lb 16 y/o.

Regarding righting the boat- you'll need a righting pole and possibly a righting bag as well to pull it back upright. You couldn't right the H16 on your own either so which is supposedly "easier" to right is pretty much a moot point. If you plan to sail solo in heavy wind, sail carefully and only in an onshore wind! I've taken my G' out alone with only the mainsail when it was everything I could do just to keep it under relative control, and had some very wet and wild rides. But(!) I always did it with a sandy beach not far downwind of me.

I'd go for the TheMightyHobie18, and try to find someone to show you the basic tuning principles for it. I believe it will be a much more enjoyable boat for you.