
Here's the situation: I'm an American and I came to Spain in July of 2016 to take a one-month TEFL course. I met DH (British citizen) on the course; he had decided to teach English in this city in Spain because he has several family members living here already. I went back to the US but returned to Spain a few months later on a student visa and moved in with him. We got married in June 2018

Because we teach English, contracts are normally only for the school year (about Sept-June). Because of this, DH has been leasing the apartment since Aug 2016, but we have returned to the US/UK each summer to visit our families. DH's contracts are from Sept-Dec 2016, Mar-June 2017, Sept 2017-June 2018, and Oct 2018-June 2019. Also, we've only been working about 12 hours a week each (although this should be going up to about 16 each soon).
We haven't had the money to take Spanish lessons, but we're looking into it (my Spanish is decent but DH's isn't good

Documents so far (translated into English):
- marriage certificate
- our passports
- photocopies of my student residency cards (valid from Dec 2016-2018) with our address on it
- both of our residency cards (his from Feb 2018 and mine from June 2018) with our address on it
- part-time work contracts for him (starting Sept 2016) and for me (starting January 2018)
- his most recent 6 payslips
- Spanish government letter showing how many days we've worked in Spain
- Spanish government certificate saying we've both been registered at this address since Mar 2017
- apartment lease with only his name on it
- letter from landlord saying that we both live here and for how long
- a few Spanish government letters sent to our address over past two years
- utilities: his name on gas bill since Mar 2017, mine on internet bill since Sept 2017
- bank accounts: his from Sept 2016, mine May 2017, closed his/turned mine into joint account June 2018 -> 6 months of bank statements from joint, and letters that show when we opened the other accounts??
- my private Spanish health insurance
- our cards showing registration at the local health center
- certificate of attendance from the TEFL course we met on
- library cards from local public library
- 10 pictures of us over the last two years in Spain with his local family and our friends, England, and the US
- cover letter explaining our situation/with table of contents of supporting documents
Questions:
1) Do you think the fact that there are gaps in DH's employment history will hurt our chances?
2) When should we apply? DH has a new contract starting Oct but he's been effectively contractless since June. Ideally, we'd like to be in England and have applied for my residency card before Brexit.
1) Do I need to add/remove anything from the list of supporting documents? Boarding passes from our travels together? Letters from local friends and family? How much is too much?

2) How do I organize the supporting documents (folders, binders, etc)? When do I submit them?
3) Once I'm in the UK, do I need to do the Surinder Singh application again to get a residency card? I'm a little bit confused about this process.

4) Can (and should) I get an EHIC?