A lot of US cities always struck me as almost like two cities that really only share a geographical border. You step across one street and you're in a different world.
My experience is in NZ so there may be a few differences (it'd blow your mind how unregulated the market is over here), but I'd say that as long as you can service the mortgage you can't go too far wrong simply by being on the ladder. Your first property need not be your last, and you can always use the capital gains and amount of principal you've paid to get yourself set up in a nicer place down the line. Just find a place you can afford and you'd be happy living in for a while (so not somewhere in the ganglands or without somewhere to park and so on) and I honestly don't think you can go far wrong.
You can also use your existing equity as a deposit for a second or third property, so simply being on the ladder counts for so much. A few years ago I bought a house in a crappy part of a small town, and now I'm using it as a rental with a ridiculous yield and I can now buy a house worth twice as much as my current one (and still keep the old one). Pool that with my fiancee's assets and there's a really good chance we'll be living in a million-dollar house by our mid-30s. It can take a while for things to get rolling, but I can't say enough about simply being on the ladder.
There may be differences in the US, but from a bank's perspective there are two parts to assessing a borrower: borrowing amount (how big a loan you can take out, which is pretty straightforward for a first home) and servicing (in which case they'll have their own formulas that are usually proprietary so it's hard to know exactly how they're calculated and really the best way is to apply and answer their questions and hope for the best). Most NZ banks will just take a few payslips as proof of income and ask about your debts and ongoing expenses (how much credit card repayments cost you, car payments, insurance premiums, how many kids you have, etc). Australian banks used to do that but just recently started also asking for other expenses like how much you spend on KFC and beer and that's made things really hard for buyers (first-time buyers in particular), so I'd imagine US banks are somewhere in between.
A mortgage broker here recently sent out a bunch of approval requests and found that the balance of your credit card doesn't actually matter to banks when factoring the loan you can service. They assume every credit card is maxed out, and I'd be surprised if the US banks did it differently, so reducing liabilities (paying off loans altogether and getting credit cards cancelled and so on) should be something you get serious on right away.
The point
@JoeyFlex5 made about winter markets stagnating is true not just of Maryland or the US but of the world. The downside is that there are fewer listings available but there are also fewer buyers and the listings spend more time on the market, so if you can knock a few thousand off a vendor's asking price that can count for a lot in the long run.
If you like, I can go into more detail about the determinants of the property market if you want to try and pick an area that's likely to grow in value, but hopefully all this helps anyway (or is at least somewhat relevant).
