Here's a few you may want to consider...
1) Read through the financial statements to see how sound the Condo unit is in terms of balance shet, upcoming expenses
2) Ask your realtor to see a history of assessments to see how stable it has been.
3) HOA fees for condos may include different items - understand what is included and what may cost you extra (eg roof, painting, Cable, Utilities)
4) Read CC&Rs association rules) to ensure they meet your needs and expected usage
5) For older condos, consider there may be expenses with updated plumbing, sewer repairs, roof replacements, A/C replacements
6) Have a lawyer review documents
Finally, be open and talk with your real estate agent about what is important to you - the more information you provide to them, the better job they can do for you. Best wishes in your vacation home hunt!