Until I get a new retainer, should I wear the old one that went through the washer and dryer?

I would certainly recommend braces for you.  I would recommend getting the chipped tooth fixed after your orthodontic treatment.

Your orthodontic result seems within normal limits. Some over jet of the front teeth is normal. Retainers will not correct this but will keep your teeth stable. You may want to visit with your othodontist if you still have concerns.

Wearing your retainers may not be a problem and may help move your teeth back into position, however, if they don't go into place with minimL effort I would encourage you to return to your orthodontist for an evaluation. Take your retainers with you in this visit.