Similar to what Rodney Dangerfield used to say, the Philly area gets no respect. The important thing to understand coming from another country like Texas
is that you are not moving to a city so much as to a region. And, taken as a whole, that region has huge opportunities for sailing over a very diverse range of conditions.
I keep my new (to me) keel boat in the Delaware at Essington. The currents run fast, and tidal swings of 6-8' are typical. But given the dozens of times I've run down to do little projects, I am glad the boat is only 15 minutes away. We'll see how much I like sailing in the Delaware this year, and then decide whether to move somewhere else next year. But so far I think the Delaware gets a bum rap. It's a lot deeper than the Chesapeake, and terms like "Philthydelphia" are a too-easy cheap shot.
Philly is about 1.5-2 hours from the upper Chesapeake tributaries, home of some of the most popular sailing spots in the US with hundreds of great anchor spots and land-based destinations. Northeast, Bohemia, and Sassafras Rivers, Havre de Grace at the base of the Susquehanna and Rock Hall are all within easy reach from Philadelphia, and there are many charters available in the 30-45' range. Here's one example - everyone tells me these guys take good care of their boats:
Bareboat Sailboat Charters on the Maryland Eastern Shore of the Chesapeake Bay
If you go east to the Jersey shore, there is sailing in the Barnegat Bay. It's notoriously shallow, which leads to some huge chop, but there are people who do sail both daysailers and even cruisers there, and it's a neat resort ambience. And, of course, you can get out to the ocean from there, Atlantic City, or Cape May if you want really hard core sailing. Someone here posted this link to an interesting daysailer rental place in Barnegat Bay:
Sailing Schools, Sailing Lessons, Sailboat Rentals and Sailing Charters at Nelson Sailing Center
If you want lake sailing, I've sailed dinghies in Lake Wallenpaupack for the last 10 years - about 2.5 hours north of Philly. There are lots of sailboats up there in the 22-27' range, but not many commercial charters. (There may be some low-key private charters - haven't really looked.) The lake is 14 miles long and up to 1.5 miles wide, with lots of coves where you can anchor for the day and swim. It's about 40' deep almost everywhere, so almost impossible to run aground. Sleeping overnight on the boat is supposed to be prohibited, but I hear people do it all the time. If you're going to be here for 3 years, you could consider buying a trailer sailor and taking it up there.
If sailing is really important to you, I suggest you move to a suburb in the direction in which you'll be sailing. If you want Barnegat, living in the Jersey suburbs will put you an hour away. If you want Chesapeake, move to Delaware County in PA (or even State of Delaware) and you'll be close to the bay. If you want to sail the Delaware near Philly you can pick almost anywhere to live.
However, be prepared to pay income tax - both to the State and a significant wage tax to Philly if you work in the city. The Philly wage tax was a very unpleaseant surprise when I first moved here (from Texas) 25 years ago.