In a 27', you may still be able to handle the rode
by hand. I did, for 10 years.
If you sail alone and you are going to anchor a lot then a windlass is a good help and make sure your anchor self-launches too. You will only need a very small model to do the job on a 5/16 chain and say a 22 lbs anchor. Lofrans
is one decent make to consider.
Some winches are installed all above the deck
(motor in the housing) and these are my faves for ease of installation
Just my 2 cents. Countless other good options too.