Sad but true but most cities don't follow the FCC's PRB-1 "recommendations" for "reasonable accommodations".
My city is pretty liberal with allowing towers and antennas to be put up but the HOA is a voluntary surrender of those rights.
My first suggestion is that I have a friend in an aggressive HOA who puts his wire antenna up and down each weekend. He's driven mounting posts into the ground and slips 20 foot PVC pipes into them Friday night and takes them down Sunday night. He guides the poles to help support the weight of his windom antenna.
Secondly, I live in a very light-wight HOA and have a nice white stick (painted black) about ten feet above my roof's peak. From that mast I have a wire antenna leading back to my backyard's tree. I have a pulley on that end that allows me to lower the antenna whenever I want for maintenance. Nobody has complained. I've talked to my two neighbors across the street about being able to use my station in the event of an emergency and they're both hip to that idea.
And finally I'm thinking about setting up a DXpedition location in the "bad lands" about three miles away. There's a place where I could hang a long dipole between two hill peaks with a large flat space in between for my mobile. I've got to go out there and laser the distance but it's likely 250 feet. I'll drive two lengths of rebar into the ground for mounting points for my paracord and pulley setup to suspend the antenna up 50-75 feet up above the truck. I don't have 206 feet on my property but the city park is the next best thing.
I'll carry my city issued RACES ID card so if there's any bothering officials I can counter their stupidity.
Stealthy 2M/440 antenna.
Tiny G5RV antenna.