So ghetto,replete with all the baby mama drama, LOL!!!

If he has any sense, he will just enjoy what he has two or three times per year and not get greedy. Don't goof up a good thing.

Yes there is a major age gap. Him 60 she 34. Only goes 2-3 times a year for 1-2 weeks.
He's soon to be retiring and has told her she'll need to be in a budget soon. Not sure how she feels about that either. As he's been her sugar daddy for so long
I doubt that she's going to give up her younger Cuban novio for him,he does know that she has a Cubano who takes care of her physical needs ,right.

OH I've tried to tell him that but he has blinders on and not sure how to shake it out of him

Yes there is a major age gap. Him 60 she 34. Only goes 2-3 times a year for 1-2 weeks.
He's soon to be retiring and has told her she'll need to be in a budget soon. Not sure how she feels about that either. As he's been her sugar daddy for so long
He should consider trading her in for a younger and cheaper model. Anything older than 30 is past its shelf life.

#12... Not going to speculate as #13 is doing... Why, because no one knows with the very limited info posted.
If she has a problem, with his capacity to provide for her, considering he bought her a property, that should tell him a lot. If she bitches, dump her is my advice. He was a fool if that is what pans out. Not the first Yuma who thought with his d*ick and not his brain.
He will have to marry her. No way around this.
For the ones that don't know me... Married in Cuba in 2003, wife here with me, in Canada, since 2006..
John Wayne said, "Life is hard and it is really hard when you are stupid".
Yanqui Boy nailed it, this guy is a loser.

The age gap in that relationship for Cuba isn't terrible. Shes an older woman than most of the tourists I see with Cuban girlfriends. It's possible they could make things work in Cuba. The tricky part will be cutting from vacation spending to real life spending. Very few are going to be able to spend at the same rate as vacation. It will come down to how reasonable his spending capability is in retirement to some level. If he can spend at reasonable level that they can both do enjoyable stuff they may stay together.
But if hes retiring on $500 a month in the provinces or $1,000 a month in Havana I'd suspect there may be some issues.
Another factor is her marketability. In Cuba I see a lot of woman that age without suitors. If shes not great looking he could potentially have a long term mate and to be honest I don't see many woman 35+ in Cuba that hold their looks. Most of them seem to lose it pretty quick.
If hes legitimately married and still living with a woman in Canada (and not actually seperated with an agreement) hes gonna likely take a serious financial blow.