What you are describing sounds like a fantastic plan. Home prices have come back and interest rates are extremely low. Investing in Real Estate for the long term is a great option. I also believe the market is showing signs of stabilizing. Active inventory is down and pending sales are up. We maybe at the bottom. Now is a great time to jump in, especially since interest rates are so low.
To answer each of your questions:
1) I would jump in now. It is impossible to 100% time the market. Interest rates are low, so even if there is a little more to go down, in the long run you still could win.
2) I think rentals are good for the long term. If you plan to hold it for 5 - 7 years +, eventually the market could return to 2005/2006 prices by then.
3) I would recommend having a good Realtor and lender on your side. Banks are being more careful about renting to individuals who also have rental property. Typically banks want to see your property rented in order to qualify you.
4) There are plenty of places depending on what you are looking for. But it is important for you to have a savvy buyer's agent helping you to make sure you get the best deal possible.
Please contact me when you would like to discuss further. In addition to selling Real Estate, I also invest in it. I own multiple rental properties and can give you first hand tricks from my experience.
Jon Tucker with RE/MAX 100. I would be glad to work with you. The rental market is very good as many buyers don't have the credit score or 20% down. Others want to wait out the rough times.
The time to buy a condo is excellent as prices are down, sellers are anxious, many in foreclosure. You can get interest rates below 5%. The bank will count 75% of the expected rent in your income qualification calculations. Talk to a good lender who can advise. I have several I can email you.
If you are interested, I would like to work with you to acquire a home in Maryland. Thanks, Jon Tucker, 443.538.4316, TuckerRealty@comcast.net, http://www.JonTuckerHomes.com