There is nothing more complicated with Trump's policy. Check "Support for the Cuban people" instead of "P2P" and go on about your individual/independent visit. No need for a group tour.
Support includes staying in a Cuban home (casa particular), eating at paladars (privately owned restaurants), using Cuban guides and taxi drivers to get around, anything that puts money in the pockets of Cubans in business for themselves, not working for the state . Your schedule has to be "full time" (an undefined term), but it always had to be under Obama's rules as well.
There are a couple of expensive hotels that are now on the off limits list, and many that aren't, but if you are going to support Cuban people, as well as add depth and cultural richness to your trip, you'd stay at a casa particular (B&B) owned by Cuban entrepreneurs anyway.
Not even many of the businesses on the "official" US government off-limits list are actually off limits. For example, if you do not buy your rum directly from one of the off-limits rum makers, but through a third party such as a shop, there is phrasing in the "new" regs that allows for purchase of even these products. And only a couple of brands are on the list, not all of them.
No one, neither CBP or OFAC, is checking when you re-enter the US, and no one has been audited by OFAC.
Rather sad that the mere perception of changes seems to be discouraging US passport holders from traveling to Cuba. The very Cuban entrepreneurs who Trump stated he wants to encourage are those currently reporting significant loss of tourist income.