Everyone seems to have their favorite time of year to visit the Virgin Islands, and I'm surprised that you haven't gotten any response to this inquiry. I live here so I will give you my basic theory: The temperature stays the same throughout the year, with the trade-winds being stronger from mid December to mid June. This gives the perception of June through November being hotter. Usually we have 10 minute Tropical showers through out the year. September through December and again in April and May we tend to see heavy/longer periods of rain fall which causes water to collect and breed mosquitoes within a 9 day period after the heavy rain fall. If we continue to have periodic heavy rains the mosquito population continues, otherwise after two weeks they die off. When the mosquitoes are active, not wearing perfume, using your favorite mosquito deterrent, and staying inside during the hour before sunset, usually will make life easier. As far as planning for a vacation in a Hurricane: We have been mostly hit in July, September and November. The advance warning system works fairly well so we know three days ahead of time when to duck and take cover. Most systems go North or South of the VI and you will experience several days of rain and overcast conditions. If a system is indicated to hit the VI . . . Get on a plane and go home, because it won't be a vacation after that. I've sent you a PM.

Personally, I would select July over later as the storm season picks up approaching September so the chances of bad weather or worse increase. It appears you are well experienced with monsoons etc. but why tempt fate on vacation? As RockyDock mentioned, the bugs are normally an issue if conditions are right for them. Prolonged wet periods followed by hot days make for a perfect breeding ground anywhere so the VI are not immune to them. They prefer still air and cool areas so avoid that sheltered shady spot behind the rocks or amongst the trees when on the beach. Better to bring and use an umbrella.

Given the size of your party and desired length of stay, your housing choices might be limited although not as much as during the high season. I would not select a villa based on location for internet or power loss as when it goes it tends to be island wide. Locals should have better information on this but during our last trip power was lost on STT and STJ was down for 18 hours. If your business relies on you being in constant touch you might need to do more research to minimize any possible disconnect but nothing can really insure against it.

Better to select your villa on what you want to do or how you wish to experience the island. If you want access to local shops, STT, more night life, etc. than closer to Cruz Bay is suggested. If you want more of the 'old island' feel than the Coral Bay area is better. You mention being used to hot and humid areas so if AC is not mandatory make sure you are in a more elevated area facing East to maximize sea breezes.

We are visiting mid June thru early July so perhaps we will see you in town or on the beaches. We will be the middle age couple, old looking man & good looking wife with stupid smiles on our faces. Have a wonderful trip and let us know if you have any other questions.

Like that answer, husband!
😉