Thanks all for your feedback and comments on the plan. I here your thoughts with all cards being from only Chase. This may be a problem for some but not a problem for others. When I a chance, I'll add in a PLAN B with gives secondary options is the first PLAN A doesn't work. I was originally going to do this but got tired and decide to just put it out as is. My feeling though is that you can not stretch the Hilton Honors points very far like you can stretch the Marriott Rewards points. Points redemption with Hilton Honors has really increased drastically recently especially for rooms that accommodate families which are usually family rooms or junior suites. I am really BIG into stretching points. As a young family we are not always looking for luxury but just FREE nights. My blog is written to meet the needs of the leisure traveler, families with children and just the average Joe. People like myself are usually pretty content with Category 1, 2, 3, 4...... and don't require high end properties for redemption. We are just pleased to go and travel for free or close to it. Once and awhile splurging with miles/points is nice but most of the time stretching your miles/points affords your family many more adventures. I am planning one such trip to the East Coast and using the 70k Marriott score to stay for 11 nights free with my family. You can't beat that for a "pack of gum"!
That all being said, I'll post some other options if the newbie runs into trouble with the Chase approves but I would recommend trying this route. Two of the three credit cards you need to get to accomplish your goal are what I like to call "pack of gum" offers - first use purchase receives the miles/points (no min. spend) and free first year. This is as easy and free as it comes. I rarely want to pay for my miles/points. I love them FREE!
Please post more suggestions if you have them. They are great!

Regarding the Citibank checking and 1099's
There are plenty of thread about that subject which I have been apart of in the past. I have done several checking accounts with Citibank and have never received a 1099. I do think that it has happened on a few reports. I'm just not 100% sure on that. My experience is that I haven't received them, so I just can't say.