One question, how many backpacking trips do you think it would take to acquire the skills necessary? I have done quite a bit of hiking/bouldering in my life, but have never taken an actual backpacking trip. I guess I just feel it is something that calls to me.
On one extreme, you can acquire the skills necessary in zero overnight trips. My first backpacking trip was 14 days unsupported with no resupplies. We traveled about seven miles bushwhacking each night with no maps. This was in military survival school. We were taught all the skills in a base camp before the trip.
My second backpacking trip was a nine day solo winter trek in Yosemite Park. This was also without resupplies. This one may not have been too smart, but I was young.
On the other extreme, you can take a year or two of practice and preparation.
Since you asked for a number, I'll give one. Five one or two night trips where you learn your equipment and how to navigate. Two 75 mile trips with a resupply or two in the middle. If you will be traveling in especially hazardous areas such as the desert or if you will be traveling in the winter, it may take more preparation. Remember, it can be winter almost year round in some mountainous areas.
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