I have done that trip on a 46'
Trawler from
NYC 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.