Although I think I have cruising in my blood, we find ourselves 1,000 miles from the nearest ocean!

In my infinite wisdom, we moved from SoCal to Denver, CO and AFTER moving here, picked up scuba diving and a thirst for more sailing. Duh. I ain't the smartest tool in the shed. So to speak.
We've sailed in SoCal when we lived there (via sailing club: 20 footers through 45 footers) and did a bareboat in the VIs about 10 years ago.
Now... I need to get on the water. We have two options given where we live and our family status. Which sounds best to you?
FACTS:
3 kids (ages 6, 8, 9) with soccer / baseball / school / etc.
About $5k to spend, although we could tweak that if needed
Option I
Buy a small daysailer - 15 to 17' (Hunter 170, Capris 16.5, Whaler Harpoon), leave it at a 1000 acre lake about 5 miles away and just mess around (after school, weekends, etc.)
Option II
Buy a slighter larger daysailer (25'-27' Catalina / Oday / Etc.) and keep it up at a mountain lake - 1.5 hours away.
I like the idea of a bigger boat and the possibility of sleeping over on it, but we may not get up there as much as I hope. Alternatively, daysailing a 17 footer seems like it might get boring (flame on!).
Anyone gone down either road and have advice for us?
(I'd really like to get a 40' Hinckley and live in Newport Beach, but absent of a winning lottery ticket, the above two options are the more likely options!

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