We are still structuring our first product - so it will depend, but we have options for all of these questions. From the securities side, we might consider Reg A+ or other crowdfunding regulation. I'd look into the structure Masterworks.io uses to learn more (I've in fact discussed this with their GC).
We've been building our beta with accredited investors under Reg D.
For others (like me) that haven't heard of Masterworks:
Masterworks creates a Delaware LLC issuer (taxed as a partnership) and files an offering of ordinary shares with the United States SEC under Regulation A. Each issuer will use proceeds from the offering to acquire a single work of art and title to the artwork will be contributed to a Cayman Islands segregated portfolio company for the benefit of the issuer. The issuer will have no indebtedness, no other assets and will conduct no operations other than relating to the ownership, maintenance and eventual sale of the artwork. The issuer is administered by Masterworks pursuant to an administrative services agreement that provides that Masterworks pays all ordinary and necessary fees, costs and expenses in exchange for membership interests in the issuer.
The Regulation A amendments from the JOBS Act ("Regulation A+", circa 2015) are indeed more recent than my last look at this, so I can't comment further. The Cayman Islands domicile rubs me the wrong way, but that may be out of ignorance.
We've been building our beta with accredited investors under Reg D.