That looks close to what my outside shoe looked (last winter).
Inside was thinner, but on top of that it was very brittle.
While I was in the process of pulling the pin holding it open it closed (back to tension) and the out side portion cracked. It was not a full snap back (I caught it part way). I also went with the CYCO tensioners.

 

My outside tensioner looked like that at 30,000 miles. The inside shoe was shot and literally fell apart in my hand when I removed it. Went back with Cyco shoes.

 

Your shoes could go another 10k,or disintegrate tomorrow,they look slightly less worn than mine at 49k kms. Not worth the risk,time for new ones and a set of cams while you are at it,I'm working on installing new Cyco's, Baisley kit and Andrews 26 cams as we speak.

 

Ever considered going over to gear drive and just forget about replacing tensioners? Just a thought is all ...

 

Outside shoe tension spring is in the direction of cam chain travel. Inside shoe tension spring is against the direction of cam chain travel. Poor design.

 

Like said earlier, its the inner one to be more concerned with...At the least replace them, better: 08+ SE cam plate w/ hydraulic tensioners or gear drive. Your already in there, get er done

 

how difficult is it to change out to a CYCO tensioner?..I imagine the outer is easy but the inner scares me..im pretty mechanically inclined ..anything special I need to know or do before I try this?.

 

Two critical things pump alignment and making sure not to shear the o-ring on the bottom(scavage). I had to do mine twice. Also having proper tool for pulling inner bearing's. It's better if you have access to press for the outer But bearings been done with out them. We have a huge arbor press at work that I used.But that's if you change bearing's too. That's what went bad on mine outer. The inners can trash the crank if the go, so it's recommended to atleast change those to the better full bearings.

 

I align with out tool also to not shear o-ring. Tip from this site, was not to put pump on first like book says but to install with out o-ring then cam plate this is to get it aligned. Now snug four bolts take off put o-ring on with oil, now reinstall, get some bolts on plate. Now this is to fine alignment crack the four pump bolts loose and turn motor over a couple of times so pump can find center. Good to go but check o-ring with a dental mirror as you can see if it was squeezed out with out it. It's to hard to get pump straight on with out the cam plate.

 

If I'm just replacing the tensioner why do I have to unbolt and remove the 4 bolts that bolt on the oil pump? plus I have to remove the tank for other work so I'm just gonna remove the rocker covers and remove and reuse the stock push rods..