I have done that trip on a 46' Trawler
to Petoskey. At 10knots cruising speed we did the trip in a month with only a few overnight runs, most nights were anchored or docked. However, we could make 10 knots straight into the wind
As for challenges you are going to have to drop the mast
to get thru the Erie canal as the clearance is someplace in the 20' range. You will also need to check your draft
as with 5' of draft
we were tight in some places in the Erie canal. You will want at least 3 people on the boat going through all the locks on both the Erie and Welland canals. 1 to operate the boat and 2 for line handling. The lock walls are extremely, extremely rough. Several 4x4 or 6x6 boards lashed vertically make good, disposable fenders.
Search for Great Loop Cruising and you will find all sorts of useful information from folks who have made the trip.