I take my family of 4 to Hawaii every year for 10ish days. Have been for several years now. I don't pay for the flight, I don't pay for the hotel and the rental car is free. 10 days in hawaii, just meals. (this year I had 5 of us and 2 hotel rooms)
The funny thing is, I am a professional Hacker that travels.... So this thread works on a couple of levels.
Here is what you do. Stay in the same hotel chain, EVERYTIME. Book flights on the same airline and since you are going out of CMH you want to use something that does hub-and-spoke service out of CMH.
Why? Because you get credit for every segment you take. So if you are flying to Atlanta, its better to use United because you go to ORD first, this means a round trip is 4 segments. If you fly delta, that is only 2 segments. 6 round trips and you are almost the first elite tier, or you can be 1/2 way.
Elite tiers build miles faster. I get 500 miles to fly to chicago and an additional 500 miles in rewards miles, totalling 1000. I am 1K on united (flown 120,000 this year so far).
I use the United credit card because that is where I need points the most. For you it might be Hilton/Marriott or whatever.
Figure out your goal and focus on that.