Picking a program

So, while I wait for my shin splints to go away, I am trying to pick my "do-over" plan.  I have debated the couch-to-5k program, but I have some concern that I could hold myself to that low of a level.  I suppose this is going to be a concern no matter what program I choose.  I have proposed to my son that he join me (he likes the idea) - I figure that will help me to stick with the "as-written-on-paper" plan.

Running this is going to be very frustrating.

Alternately I have thought about starting out with 1 mile runs, 5 times a week.  Then move it up to 1.5 for the following week.  Then 2, then 2.5, then 3.. But I think that this might go beyond the "Start over" idea - and do to much to soon. Especially if I keep raising it by .5 miles. 

I thought about this same pattern of running a set mileage and increasing it weekly - but using the 10% rule.  Start at 1 mile, then go 1.1.  then 1.12 the following week. then 1.23.  The big problem I see with this one - is that it almost requires my runs to be on a tread mill.  In addition to my hatred of those things, it will not get my bones/ligaments/muscles used to the pounding on pavement - which is one of the primary reasons for "Starting over."

I am definitely open to any suggestions!
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Next years potential running schedule (goal of at least one race a month)
Jan -
Triple Cities Runners Club - January Freeze 10k Series
Feb -
11th - Cupid's Chase 5k Run
March -
39th Annual Forks XV (15) K Run
April -
Mudders and More Trail Run and Family Walk (if it is done again next year)
May -
6th - Greater Binghamton Bridge Run Half Marathon
June -
Tortoise and Hare Trail Run - Buttermilk Falls Ithaca
July -
8th - The Utica Boilermaker
August -
Kelly LeBarre 5k
Sept -
Monstar Marathon and Half Marathon Trail Run (unsure of which I will do)
Oct -
Wine Glass Marathon
Marine Corps Marathon
November -
Some Turkey Trot.
December -
Dec 31 - YMCA Resolution Run