How to Regrout Stuff

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I need to get my current place rent ready.

It took me 8 hours to change two faucets. I probably should not pick up a hammer. Though it is fun at times.

My next project is to regrout my shower floor, and kitchen/bathroom counter tops. Is that even a realistic do-it-yourself project for a non contractor type. I am more of a web and software developer musician type.

I hear it's not too hard. But I am wondering if I should just pay someone to do it, or tackle it myself. Any tips a good how-to regrout stuff website?

I think my biggest fear would be the shower floor done badly, then leaking into the unit below (this is an upper level condo)