Buying condo to do short term rental?

It may be cheaper to rent a vacation unit for a month than support the expenses, mortgage, business license, insurance, maintenance, utilities, advertising, cleaning, upgrades, taxes, etc., over the course of the year.

Very likely it would be. You'll be lucky to count on maybe 12 weeks of rental a year for a good unit with good location. But there are still other valid reasons to pursue a unit. You might find a good deal now, nobody knows what the market will look like in 10 years. Condos can be renovated, perfect locations are in limited supply. You may want to use the unit several times a year in between rentals.

I don't think I would purchase a unit unless I could afford all the yearly expenses into the foreseeable future. At first we may only use it 2 weeks a year or so but hopefully going forward we would be there more often.
I will honestly be more concerned with future resale value than I will be with annual revenue. But as was pointed out, no one knows what the market will be like in 10-15 years. I'm hoping my realtor can help educate me about trends and probability, however. I did read somewhere that condo values tend to rise and fall more slowly than other real property? So potentially less upside, but also less downside?

Realtors are a good resource but will probably give you a somewhat biased opinion on anything. All property values on STX seem to move slowly in general. Of course the exception was the market going South in 2008 and on top of the the closing of the refinery. That left a lot of properties on the market, some foreclosures, many bargains to be had. But the market is slowly recovering now back to normal, inventory is down, prices are stabilizing. 94 units available today, I think we were around 150 or so at the bottom of the market. In the typical market it seems sellers tend to hold out for their price which attributes to lengthy time on market. But I think most aren't looking to sell at a huge profit but rather trying not to lose their shirt. The good news (for buyers) here is we don't have a hot market driving prices up and up and up, at least not yet.

We have a big range in condo prices with of course the usual many factors, location, condition, views, amenities, unit size and features etc. New listing today for ST C 1BDR for $110K, looks like in decent condition but priced to sell. There are condos for under $100K but probably not something suitable for vacation rental. And of course we have them up to $1.5M and all in between.

Thx for this info everyone...myself, just a basic question, is it feasible to think I can find a condo for under $150-200K on St. John, and if so, what would it more than likely consist of?

Thx for this info everyone...myself, just a basic question, is it feasible to think I can find a condo for under $150-200K on St. John, and if so, what would it more than likely consist of?

Doubtful - you'll need to at least double the higher end of your budget to find even a basic very small "efficiency" or perhaps 1 BR condo.

Not likely to find something in that price range in St. John.
Even if you double that budget.