Rent a sprayer if you choose to spray and do not have a higher output sprayer on hand. But keep in mind not having used one that figuring out the machine and settings for you to be able to lay down a nice finish could take some time. Also, do you have the space required for spraying and drying. Maybe you could prep them all and have someone that has spraying experience spray them? Brushing can get you some pretty nice results as well depending on products used, brushes, application skills etc. They are shutters that are not going to be in high visibility areas where people are going to notice spray vs. brush (unless they look really bad) so you should be fine with brushing them.

Yes that is fine if you are going to black. Tint your primer. Even if it is a dark grey would be good as it does not have to be black. Black is becoming more and more of a star on things and people are really starting to like it once they get out of this everything trim related has to be white that many people have a hard time straying from. Black is sharp in my opinion.

What paint stores do you have your area that you are available to buy from? What type of wood are the shutters? How many bare areas will be present after scraping loose stuff off and sanding? I would recommend a semi-gloss or satin sheen in either a 100% acrylic or a waterborne hybrid. Both will stand up fine and look nice. It really is a matter of preference on if you like more sheen or less on them. Benjamin Moore, Dulux/PPG, Sherwin Williams. They all have high quality top performing paint lines. Can't go wrong with Aura from BM, Dulux Diamond line is great too. Nothing is going to be bullet proof and withstand the harsh environments forever and they will all need to be recoated down the road (timelines dependant on the direction facing and extremities of the weather. Just use the proper primer and a high quality top coating system and allow for proper dry times and re-coat times throughout the process and make sure your temperatures are high enough for allowing for a proper cure.

If you are going to paint the outside id recommend buying a good sprayer not a hand held but one that has at least a 25ft hose and you can use it out of a five gallon bucket they can be time consuming to clean but will make the overall job easier. Make sure all the prep work is done right pressure wash it as good as possible and allow at least a day to dry. when working with the shutter like you said scrape and sand down as good as possible if you are not going to prime the whole surface It is very important to spot prime areas that are bare wood or the paint was scraped off of this goes for the house as well . Since the shutters are wood you can go with a peel bond primer from Sherwin Williams one of the best for painting wood serfaces for harsher weather or a multi purpose primer from Benjamin Moore or Sherwin Williams. Since the shutters have some peeling and missing paint spots id go with a satin sheen so that it gives a better finish and does not high light imperfections like a semi gloss or gloss would. For exterior paint Benjamin Moore, Moore life, Moore guard, and Aura are great. From Sherwin Williams id go with Duration or Emerald.

This is great - thanks so much for the suggestions and direction. Keep them coming - I'm taking the most practical route and I really appreciate product recommendations.

Dulux Diamond was my top pick for my 80 yr old shingled house and shutters. We live in Nova Scotia, Canada so extreme temps from summer to winter. This paint really holds up...it's now been 5 years with minimal touch ups. Plus you can paint when temps are quite cool. The spec sheet will give you temp range, but it was helpful that you can apply quite late in the fall and the paint cures really quickly.