You are getting some good feedback I see from several professionals. I would like to add just a couple of options for you to consider. I am with Coldwell Banker Residential Brokerage in Milford, CT and we are the #1 Brokerage Firm in the area. The easiest of your questions to answer is the size of the condo. A 2 bedroom will bring you a much larger buyer pool when you go to sell than a 1 bedroom for the reasons already mentioned. The second easiest question is whether now is a good time to buy. Interest rates are still at historical lows and inventory is up. Now is a great time to buy! The hardest question is the location. Even though you have mentioned some personal choices, there are still a lot of considerations to consider. I would highly recommend you select a Realtor that you feel comfortable with and you feel will have your best interest at heart and then review the options in a few different locations to see what feels right for you. Milford has a great downtown and great beaches but I would also consider the West Haven area near the beach as there is a lot going on there, some up-and-coming areas and you are still close to New Haven. I would be more than happy to assist you and email you some properties or you can get automatic daily updates sent to you from my website below.
I wish you well and look forward to hearing from you.
Coldwell Banker Residential Brokerage
"Don't Buy or Sell on a Whim... Rely on Tim"
Have you considered Branford?
It is a great shoreline town, lots of people in your age group, gyms & restaurants and beaches! Branford is within 10 minutes to New Haven too.
There are a few options in the 100-150K range that I can email you to check out.
Two bedroom condos are a better investment. When you go to sell you will appeal to a broader market. (Professionals that want a home office, small families, etc...)
Let me know if I can help in your search and if you would like to see the list of condos available in Branford!
Kimberly Bailey Madelung
William Raveis Madison