I began selling in year one and never looked back. In year 1 I started with 27 taps and quickly got up to 79 taps. I only sold syrup at work (at the time I drove school bus after selling my business and not being ready to really retire). I only made just under 11 gal and sold all but 3 gal, all in smaller sizes. By year 2 I'd added over 100 more taps, gone to gravity tubing, built a 16x24 sugarhouse and sold my "half pint" evaporator and bought a used 2x6. From then on, until 2018 I added more taps every year and sold most of what I made, I never went for the bulk sales concept, the only bulk I ever sold was B grade and later on an occasional very dark, but that stopped too as I started making bourbon barrel aged maple syrup, a real winner.
Don't be afraid to sell your syrup, if it's good enough to give to friends it's certainly good enough to sell. Besides, if you sell it, keep all receipts, they can then be claimed.