A J-pole mount actually is less reliable in higher wind areas than a traditional tripod or chimney mount. A couple years ago a strong thunderstorm and "redirected" my J-pole mount. I had it tightened down beyond sufficiently however, mother nature bent metal and I had to remove the J-pole.
There is also a consideration that a J-pole isn't going to be adequate for mounting a DB8e and HBU11. Normally, the J-pole is fine with smaller single antennas. Larger, stronger antennas require more room, plus you need to be able to ideally have 6' or so of accessible pole space to mount the DB8e on top, and 4' below HBU11. A single J-Pole isn't the way to go in this case. You can see here that the DB8e uses all the space available:
You could add a second J-Pole with the HBU11 4' away from the DB8e. The 4' away distance is important because if the antennas get to close they can alter each others reception properties.
A stronger more weather tolerant system though would be similar to what I have installed with a roof mounted tripod:
Or chimney mount:
For this recommendation, I am not going to suggest a mast mounted preamp. Instead, the DB8e and the HBU11 will be combined via a mast mounted Antennas Direct EU385CF combiner. This takes the VHF signal from the HBU11, the UHF signal from the DB8e and combines them into one lead. A preamp is often recommended on the mast. In your situation with three splits of the signal I often prefer to make sure each split is getting amplification at the split instead of pushing it down from the mast through the splitter.
The distribution amplifier you'll need will be a Channel Master 3414. This will reside in your house at your point where the signal gets split three ways. The nice thing about the CM 3414 you'll have an option to add a 4th feed off the antenna system in the future due to it being a 4 port unit.
Your elevation is good, it's just settling on the mounting system that works whether you go with 2 J-Pole mounts 4' apart then combined via a EU385CF, mast mount or tripod mount. The antennas are the easy part, it's the installation that works for you.
With the antennas outdoors, all of Hartford should all things being equal be reliable.
Cheers.