As a professional sound person, doing both live sound and transfers to digital, I say you can do it however you wish, but there are some important things to consider:
Proper playback is the most important thing, and (especially with older tapes) aligningthe head to the tape can be the thing most often unkown. If the head of the playback deck doesn't match the one that was used to recordit, the teble will be affected and the sound muffled to some degree. I use Makamichi decks with variable azimuth alignment, and adjust it to each individual tape before ruinning the transfer. This can make a huge difference in the sound quality! Even a good deck that runs well can be misaligned compared to the cassette.

There are many other factors that can make it better or worse, and as a professional it pays to do it as well as possible. ALWAYS the most important factor is the best playback you can get.

Of course I'd say take it to a pro, but details do matter! And cheap machines will sound cheap, and if you plan to digitize and listen to it a lot, do it well from the start!