Besides the architecture/construction considerations (building code, finding a contractor that know how to work with containers, etc), does anyone has any experience with these, specifically in terms of financing and insurance? 

The Gulf is never leaving our island so we will always have strong STR numbers.

Strongly suggesting you start right now, regardless of which post you stationing at.

Rents have to be strong (1%+), great location to major travel routes, great amenities, great schools.

I am seeking a small group of folks that can do the same and add to skills and resources I don't possess or am not strong at, and take some of the load off/ shift some of theirs.

(Forbes)Lower business & lifestyle costs than others.Amazingly affordable real estate for investment.Single-family, duplexes, fourplexes.3-year appreciation forecast of 9.1%.Around 45% of the residents are renters.The growing fuels the rental demand.San Antonio is also known for its low cost of living.Closed sales increased by 14 percent year-over-year.Compared to June 2019, San Antonio's average price of a home increased by 3%.Year-to-date, the average price has shown an increase of 5% to $278,395.In a year-to-date, year-over-year comparison, Bexar County faired well compared to Travis (-10.7%) Harris (-4.9%) and Dallas County (-6.8%.)Each of these counties indicates a decrease while Bexar county shows a promising a 3.4% increase.As predicted, June has shown to be a strong buying season.

Zoning petitions, architectural challenges, contractors, etc. 

@Kiet Tran if they are both strong rentals, why not both at the same time with the same lender? 

My background is architecture and construction, and I feel I most need to learn more on the business/legal/tax side of the process.

I would strongly consider self managing using the tools that Vrbo and Airbnb provide.Drop all this in a spreadsheet and see what the net profit could look like with a best and worst cast scenario.