For survey, I would highly recommend Gene Barnes 978-281-6040. There are many good surveyors but Gene is great. As to issues - too many to list. Get the right surveyor. Different boats have specific issues resulting from original design and build.
As to covering - people do different things. A custom cover is expensive so I would hold off a year. Most shrink. Some cover themselves. Different yards have different rules. Biggest issue is freezing water from ice, rain, sleet, can crack hoses, block scuppers and raise hell with
varnish. If you are not around to inspect frequently, I would shrink.
Its late to be looking for storage. Where is the boat now ? Most insurance companies require haul out during winter, but there are exceptions. Also, insurance companies are picky right now on age of vessel. Making sure the boat is insurable was hopefully a condition of purchase.
I'm near Boston. Let me know if you need more help.
Larry