FHA loans and marriage

[Daniel Gibson]

My fiancée and I are planning to move to Florida in Dec 2020, buy our first ever property, and we'll be getting married in Feb, 2021. The plan is to buy a fixer upper and house hack. The long term plan is to stay in Florida for ~one year before renting out our property and moving to Chicago to buy another property. 

I was originally planning to buy the property in Florida using an FHA loan, however, knowing that I can only play that card once (most likely) , I'd prefer to use an FHA loan to purchase a property in Chicago, where the house prices are generally higher than the part of Florida we'll be moving to. Given I have a few options, I also have a few questions:

Scenario A - I use an FHA loan to purchase the house in Florida
Q: Can my soon-to-be wife qualify for an FHA loan if I already have one after we get married?

Scenario B - I use a conventional loan to purchase the house in Florida
Q: Can I qualify for an FHA loan if I already have a conventional loan?

Additional context: 

• - I have a good credit score ~765
• - I have ~$30,000 for a down payment (I've been assuming I'd go with an FHA loan @ 3.5% down and planned to use the rest on fix up costs)
  - My fiancée's credit is okay (mid-600s)