I need some sage advice

Alright, I've got a few kinks that need to be worked out before I'm doing this thing long term. I could use some advice:

1) Headphones: I am having a terrible time finding headphones. I have now gone through three pairs. The problem is my ears are quite small. The tiniest of ear buds won't stay in my ears. I tried a Nike over the head design that kind of sat in your ears and those kept falling back and hurt my ears. So, I want to know...what kind of headset can I use that won't fall off/out and won't hurt my tiny ears while I plod to my podcast?

2) Feet trouble: I mentioned I thought the shoes wouldn't work because they kind of rubbed my arches. After my workout today I had a small blister forming. When I went to inspect it I noticed that entire part of my foot had noticeable swelling that looked like a large hump. Anyone ever dealt with this before? Is this because of my shoes? Is this because I'm a gazillion pounds overweight and exceeded the maximum weight limit on my poor shock absorbing feet? Is this because I've sat on my butt for the last year and all the sudden decided to workout? Or is there something more sinister at work here? When can I run again?

3) Ok, I had one more issue and I forgot what it was. I'm getting senile. Post your own advice to whatever problem you wish for number three.