I recommend hiring a private investigator. That's what my firm does when the sheriff can't find someone to serve them.

The charges might not be dropped. Even though the items weren't "his," they could still be determined to be in his possession if he knew what they...

Doesn't really matter. Cops often follow for miles before turning on lights. You don't need to still be in the vehicle when they catch up to you.

Depends on what his actual sentence was. If it was, for example, one year but suspend all but 48 hours, he could be on the hook for up to the full...

It could. Hire an attorney ASAP. They may be able to get the seized evidence suppressed.

Yes, this is technically harboring a fugitive.

In Indiana, the prosecution has six months from the date of arrest to being him to trial....

It likely won't affect your criminal case but you certainly need to file suit against the city/dept of corrections. Contact a local civil attorney...

Most if not all arrestees are subject to fingerprinting. Even when released.

Unsupervised means unsupervised - no drug tests or any other monitoring. Just stay out of trouble.