I cruised Cuba to Grenada for four seasons on a VHF, a Grundig receiver and my laptop downloading GRB files while scabbing wi-fi. I found Chris Parker to be very conservative. He is not always heard. The joke joke always was that someone said they couldn't receive him that morning and a host of cruisers would, "was it 6 oclock Chris or 7 oclock Chris? Did you turn the fridge off? Were you leaning out hte companionway with your tongue hanging out?
Weather below the Bahamas is imperfect. The good thing is that once down there, 25 knots is normal, 30 is breezy and 35 is a good day not to go to wind. The islands are 6 hours apart except for a few overnighters. Get a great SSB receiver (no license required), your VHF with a mast mounted antenna goes further than you think. We called in an emergency for a cruiser between Antigua and St. Barts and Guadeloupe picked us up without problems and St. Thomas was heard as well.
If you mean southbound when you refer to the thorny path, and you are in N. America, go south from Marathon to Varadero Cuba. Get Calder's cruising guide and go around the south ide of Cuba, jump over to Ils la Vache and then DR. Mona is a quick overnighter and then you're there.
Forget what the American's say, go to Cuba. It's not the thorny path, in fact it's a breeze. In years to come it will be the only way to get to the Virgins and the the Windwards. Do not worry too much about getting everything perfect, you'll end up not going. We had no liferaft and kept getting guilt from fellow cruisers. Our dinghy was twice as strong, always ready and never needed repacking by someone that pretended to be qualified.
Sail off young man and report back. I would like to know how much you enjoyed Cayo Largo?