Ken,
Where exactly is this community? I've lived in Annapolis for over 30 years and might be able to provide some specific advice on the area. I do own a condo as part of my rental portfolio and would offer the following warnings:
1) HOA fees can be increased, especially in cases where the Board is looking to raise additional capital for deferred maintenance (or if there large groups of occupants not paying their dues). Alternately, they might charge one time "special assessments" to cover large capital improvements. For example, every homeowner might be required to pay a one-time expense (e.g., $1000) to fix the roof. Good HOAs budget for these types of maintenance/capital expenses and ensure that their members are paying their dues. That way they don't have to resort to HOA fee hikes or special assessments. You really need to dig into the financials of the association to understand the whole picture. How much do they have in "reserves"? Do their available reserves cover upcoming maintenance/capital expenses? You should also walk the property and assess if their is a lot of deferred maintenance, which would offer more evidence that the association is not healthy.
2) You need to review the HOA bylaws in their entirety. Often times HOAs will only allow a certain percentage of the homes in the community to be rented. Additionally, they often will require minimum terms such that you can't market the property to short term tenants (not always a big deal but it limits your pool of tenants). Don't trust what the agent or HOA tells you...look at the bylaws.
3) Most banks won't offer financing on a condo if the HOA is in bad shape. Most banks get concerned when their are high delinquency rates on HOA dues and/or low owner-occupied percentages within a condo community. Disclaimer: I'm not a lender, so others can probably provide more accurate advice here.
Bottom line, you really lose a lot of control investing in condos...mainly because the HOA has so much influence on whether or not your property is a successful investment.
I love my condo...but I consider myself lucky. It was my first investment and I probably should have done more homework in hindsight. With that said, the HOA's financial standing is excellent and they keep the property in amazing shape. The condo is also in an excellent area that has appreciated nicely. BUT like I said, I got lucky.
Best of luck,
Andrew