I'm surprized no one jumped all over you for even mentioning HF. Personally i like them and have never been really disappointed, as long as i realize their motto should be "Where the customer is quality control." They truly do not argue about the 90 day money back guarantee, as long as you have receipt and the trip to return or exchange item is not too long or out of way. I am leery of their battery powered tools, tho haven't bought any.
Others have said that rolling and brushing is going to be faster and easier than spraying. And that is true. Masking and taping off, then cleaning sprayer is most tedious part of spraying, as well as masking off yourself, hair, face, eyes etc. And even gentle breeze will carry overspray to neighbors house and cars.
Compare pressure and cubic fet per minute, CFM, needed by sprayer to what your compressor puts out, specifically CFM at needed pressure. Also size of paint pot, most are only quart or less. Some will feed from larger container with hose. HVLP would probably be best, you'll be closer to surface, less overspray to get blown.
Make sure sprayer comes with some kind of viscosity device to make sure paint is thinned enough to spray.
Have you considered airless sprayer? Buying or renting.
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