Itinerant VHF frequency and a bunch of CCR DMR (MotoTRBO) portables is what you need.
The HOA can certainly apply for the itinerant VHF frequency (IIRC its just 250 bucks) which is NOT a ham license.
And as for what radio to use, as of the writing of this post the Baofeng BF-1801 DMR/FM walkie is the cheapest option to buy bulk. Its not an XPR 7550e, but it should reach 300 yards without much of a problem on VHF without the need of a main repeater. Once you have the itinerant frequency license and the radios, all you have to do is assign each radio to its own unique ID, each ID being each house, etc... then create a talk group for the homeowners association/group, and set every radio to listen to that group, lastly assign one channel to the licensed itinerant frequency you acquired and you're good to go. On DMR you can also create subgroups, etc, and any subscriber can punch the ID of another subscriber to make private calls, so only that person will hear the call, you can also do texting as well... and can do call alerts (ringing the phone) which will leave a missed call reminder on the radio with the person who called you.. radio checks. DMR is very flexible.
The BF-1801 radio has digital encryption (not voice inversion crap), its a true 40bit digital encryption and while it won't prevent the NSA from chiming in, it will thwart the scanners and any eavesdropping.
G.