If you're happy with your current house, I'd say go with 1&2.
It's secondary properties that really start giving you investments, so having your primary paid off and being able to maybe make some money off others is an amazing place to be in.
If you do #2, and have someone covering all of your costs you can still do lots of #1 with your wages, while someone else is paying off your investment.
By the time you need #3, you'll hopefully have 2 properties largely paid off and can always sell 1 then and get your vacation home.
If you don't need your vacation home yet I don't see the point in getting it now, as the investment property in the city has a better chance of little/no carrying costs and investment upside. Let it work for you, and swap it for the vacation home when the time is right.
my 2 cents.
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