Moving to the Island in September! Starting a business?

"Our business thrives on always being on time and going the extra mile,"

That's a rare treat in the VI.
Getting known and word of mouth will be a hurdle as will finding your way around to your job sites which might be interesting as road signs, street signs and house numbers are in short supply and can't say that you can depend on a GPS to get you to your destination.

I think September is a good time to get here and get settled in prior to the start of tourist season beginning mid November/early December. Most places begin to hire in October for start of season.
Sept/October is generally the height of hurricane season, here.
Can't speak for STX but STT has many beauty, nails, hair salons, spas and the like businesses.

6 months living expenses minimum is a must.
Budget everything!
Rent, 1st, last and security, cars, shipping, business licenses (you must have one to work in any hair, nail, beauty industry) you may get away without one for handyman however advertising might be an issue without one. Best to check) cleaning supplies, bedding and linens, stocking basics for groceries, pots, pans, dishware, glassware, silverware, furnishings, small appliances, bring your tools!, groceries, deposits for utilities, the list goes on and money goes fast. It's expensive to live here.

It can take awhile to get a business license. Start early.
https://www.bing.com/search?pc=ASWI&form=AMZNS2&q=vi+licensing+and+consumer+affairs

http://dlca.vi.gov

It's better to call and speak with someone, IMO.
Get their name so you can follow up.
Good luck!

Even at the height of your success in business I doubt you will have to worry much about the local competition feeling you are trying to "take over"!
Absolutely get a business license and the proper contractor, plumbing, electrical certificates if you are doing that particular kind of work.
That will also apply to some extent for your wife in her endeavors. I ran into a young man today at the hospital trying to get his barber certificate and health cards.

Sept. is a great time to start if you are financially secure for 6 months - a lot of 'settling' here expenses as mentioned. But a better selection of available rentals and a few months of slower season to get the business organized, learn the areas and get used to the supply chain for handyman type supplies.

Low season is also when owners will be looking to get stuff fixed in their rental units before things get busy.

I'm pretty sure that your wife will have to retake her exam here to get her license. I suggest you start looking into that ASAP because I don't think they offer the exam but a couple times a year. I don't have personal experience with that myself, but my hairdresser had to do this several years back when she opened up her own place. I remember her being quite stressed out about the whole endeavor! But she is doing well now.

For you, I would also suggest getting licensed and bonded. A good place to start might be to reach out to any property management companies, condos, etc. Handymen who are knowledgeable and show up on time is a treat. Not sure what kind of work you do, but things are definitely a bit different here than they are in Indiana as far as construction goes. My hubby gets the most 'emergency' calls related to the water pump/pressure tank/and dead ceiling fans and outlets.

Although September is considered peak hurricane season, it's usually my favorite time of year here. It's quieter with tourists, but the locals are out and about. Good time to network and just enjoy the place without being super busy with work to do or tourists. Good luck!

Just check the DLCA website for all the license details, it's all there including exam dates.

Im a fairly new transplant. The rental properties here are about the same as any big us city. As far as getting a business going, if you are good at what you do it spreads fast, same as if your not good. The biggest thing it's being friendly and learning the culture. This place it's not like the states. You have to great everyone even if it's in line at the bank. Politeness is required here. And you must remember we are all on a small island, if you cross someone you will defiantly run into them again. The plus side is that mostly everyone is very warm and inviting. And this place is a paradise. I hope you do come here, message me and i will be on of your first customers