Well one sign is physical atrophy of your balls, they won't shrivel up and die, especially from something like Osta, but they may shrink a bit. You'll possibly feel less energetic and have a little worse mood throughout the day as well. You may notice less of that "alpha" feeling and be a little less aggressive with people (Maybe you aren't already though, so it all depends). You may feel all of these, you may hardly feel anything. Being shutdown isn't like an on/off switch, it's just having diminished natural test production, and this happens gradually over time, so don't expect to wake up one morning and say "oh, that's it, I'm shutdown now!".
Edit...
As for your plan, you'll probably be fine. 8 weeks is a while, but even at 3 caps Osta isn't nearly as suppressive as a full blown PH/DS would be for that length of time. The Ultra Male should get you back in shape just fine.
And as for insurance with bloods, the place recommended on here doesn't even go through insurance as far as I know, so you cant use that as an excuse