So, I'm following advice and gov't links...

In particular I'm looking for first-time Americans that hit Cuba this year, 2018. I understand some of you have been "travelling to Cuba since the Stone age", but I tend to think you might be an exception when you travel.

You definitely do not want to hear from me in that case.

Try the Cuban section of TripAdvisor. They seem to have a good number of "one recent trip wonders" over there who will be happy to tell you everything anyone would ever want to know.

Not a first timer in 2018, but not one of the veterans either.

SFO -> PTY -> HAV
Tourist Card will be obtained at check-in at PTY, right? Green Tourist Card?
I fill out 12 categories form, with SUPPORT FOR THE CUBAN PEEPS box checked, right?

If you're traveling from PTY with a green Cuban tourist card, you shouldn't be asked by the PTY-HAV airline for a US OFAC reason to travel.

According to the 'rules' I qualify for this by staying in casas, eating at casas, engaging/talking with the Cuban peeps, paying local guides for my hikes, using public taxis, bus (Viazul), buying from family-owned stores... right?
Bring health care proof of coverage
Keep a record of itinerary/schedule... and receipts...

Who owns Viazul? You do get that even the entities on the "naughty list" can be used through another party, i.e. not booked directly.
How do you tell a public taxi? Or a family owned store?
Receipts? What are those? NO ONE in Cuba gives receipts. (A restaurant may give a scrap of a handwritten bill but it disappears with your money to pay.)
Health care proof of coverage when traveling direct from the US is your boarding pass. Do you have other insurance valid in Cuba? If not, do you know how to purchase from Asistur? Do you know if you will be asked at entry if you have it? (I wasn't, on more than one trip.)
The itinerary is B.S., particularly if serious about that kind of detail. Will never see the light of day after writing anyway.

Just go and have fun. No worries.

The tourist card and the OFAC declaration are two different things - if your flights are on the same ticket, Copa may want an OFAC declaration.

As bahiana mentions, buses don't count for "support for the Cuban people".

If you are a US citizen, it does not matter which passport you use, the OFAC rules still apply.

Not sure how you get a visa from the Cuban embassy as they have NEVER returned a phone call or replied to my email.

So far as local owned, I'm thinking most business are government owned, (Am I wrong on this?) and it's a fairly recent thing to have a local owned restaurant, etc.

And by the way, has anyone mentioned the don't take USD thing? You'll be charged 13% rather than the normal 3%.

People go to the Cuban consulate in person and can get a tourist card there for $50, apparently.

Paladares (privately owned restaurants) began in the 1990s - is 25 years "fairly recent" ? Similarly casas particulares.

A lot more categories of self-employment were opened at the start of the Raul era - about 8 years ago now.

And by the way, has anyone mentioned the don't take USD thing? You'll be charged 13% rather than the normal 3%.

Doing a double exchange is only worth considering if you can get the other currency at a good price. Some people end up paying more than 10% to change in the US and so end up with less CUC than if they had exchanged in a Cuban cadeca. Others exchange their USD privately in Cuba and get as much as if they had exchaged to another currency with less hassle.

People go to the Cuban consulate in person and can get a tourist card there for $50, apparently.

Hard to do when you live 1000 miles from it.

Paladares (privately owned restaurants) began in the 1990s - is 25 years "fairly recent" ? Similarly casas particulares.

A lot more categories of self-employment were opened at the start of the Raul era - about 8 years ago now.

And by the way, has anyone mentioned the don't take USD thing? You'll be charged 13% rather than the normal 3%.

Thank you for the correction. The video I saw was three years old and stated "recently".

Doing a double exchange is only worth considering if you can get the other currency at a good price. Some people end up paying more than 10% to change in the US and so end up with less CUC than if they had exchanged in a Cuban cadeca. Others exchange their USD privately in Cuba and get as much as if they had exchaged to another currency with less hassle.

True - No one pointed this out as an option to him though. Good point on the currency rates. I saved some but could have done better with effort. I was lucky enough to change my leftover CUC to USD with an arriving Australian, 1 for 1.

PS - What's the least expensive airline to Cuba these days? Any suggestions?

Why bother trying to get the tourist card from the consulate - but it from the airline. Much easier.

I have no idea what video you saw, so cannot comment.

Airline - it is easy to call up the prices online and compare - I would guess that things vary depending on where you are coming from and the dates you want, like most destinations. Remember to factor in the difference in prices of the tourist cards. Copa had some very cheap prices via Panama recently - but I don't know if they are still there.

I traveled to Cuba a year ago with a small photo group, and then went back with a friend this February. He and I just started planning a 3rd trip today, leaving in June! I can't speak to all the red tape and cautions you've been hearing and seeing, because that just has not been my experience. Going to Cuba from the states was absolutely easy and hassle-free. First of all, a visa should be obtainable ($50 on Southwest) through your airline just by filling out a simple online form - choose the 'support of the Cuban people' category, and forget about receipts, where to shop, how to travel, etc. And your airline ticket should include coverage for Cuban healthcare, should you need it. Nobody cares about Visa requirmentsa, and nobody checks (we did some online searches looking for Cuba visa violations going back 10 years and found no infractions). Spend cash. You can prepay some bookings ahead of time - try airbnb and tripadvisor, cuba-junky, or any number of other sites. I recommend staying away from the big tourist hotels - locals in casa particulares will treat you very well. If you really want to go by the rules, avoid these businesses: https://www.state.gov/e/eb/tfs/spi/cuba/cubarestrictedlist/275331.htm.

Do you speak Spanish? Mine is minimal, but my friend speaks a bit, and that gets us by. People are patient and helpful.

Go. Have a great time!

Thanks to all for the replies...

@bobmichaels - TripAdvisor is a great resource, thanks
@bahiana77 - I will be using the Restricted List for businesses NOT to use. It states that if the business is not on the list, it is fair game, EVEN THOUGH a Restricted List business may own another business I use. I hope I interpreted correctly
@beardouk and @airemel - thanks.
@goslow - that's exactly how I want to do it, thanks. Yes, I speak Spanish and finds it has huge benefits.

I plan on $100USD/day, I'll be there 12 days, will take 1500USD. Yikes, I hope I don't get robbed.
IF I get robbed, what can I do for money? Ask casa owner to do Western Union from the States?
12 days: 3 nights in HAVANA, a few in Isla de la Juventude/Cayo Largo (Is a day trip possible if I cant get casa booking? ), a couple nights in Trinidad. I'll have a few days to be flexible.

Goals: beaches, hiking, tour Old Havana.

EDIT: I'll be there the last two weeks of this coming May.

Gracias!