You shouldn't really lap solder wires to boards. They tend to pull the pads off the boards or crack. Better to use wire to board connectors or solder terminals.
But it’s surprising how poor the reliability can be. Aside from your points, solder can wick up a cable, and then the cable often breaks just at the point where the solder ends since it has no strain relief and may be right in the middle of a bend. This is especially true for adding solder to a crimped connector “for good measure”. It does more harm than good.
That being said it’s convenient many times especially if you don’t have connectors on hand or need to place wires in a specific orientation. Hot glue or better yet, RTV silicone can be used to make strain relief to increase the reliability. Or, when using perf board like in the post, a good technique is to drill a hole for a snug fit of the cable including insulation, then pass the cable through the hole before soldering to an adjacent hole.
It’s worth expanding on my comment now I have a few minutes. You can terminate solid core like this if it has some strain relief but not stranded!.
My favoured construction method is to take a Hammond box lid and screw a piece of blank FR4 single sided copper to the inside of it leaving enough space around the edges for any (proper) connectors you need. You can then drill out anything you need, usually BNC, SMA, DC jacks, FT capacitors and D connectors for me. You build the prototype on the FR4 board dead bug and use solid core or RG174 to wire up the connectors and lap solder them to the boards or components as required. This is done carefully with thought for weight distribution and to keep the total mass of the wires low. When it works the Hammond box is closed. If it needs to withstand vibration or moisture you build it into the bottom of the Hammond box and when done fill it with potting compound.
(Through holes are fine. Mostly.)
For quick one offs, simply place a normal pad, place a copper fill polygon connected to the same net around the pad, and turn off thermal reliefs / set pad connection to solid for the polygon. Obviously if you need it a lot, draw a new footprint.
You need to nail the pad down with a few vias (under soldermask is fine) or use a through hole. Please just use a through hole if you can. They're a lot more reliable than just about anything else. Even SMT connectors rip off boards without much trouble. (This is my job. I have seen some things.)
Just stay away from any Molex crap. Tends to charcoal itself.
Solid wire through holes is OK if the wire is never going to flex. Otherwise the stranded wire lapped to surface mount pads, or soldered into through holes, with a big blob of hot glue or epoxy for maybe-sorta "strain relief" is a great pet peeve of mine - it's ugly and it breaks.
Never had a problem with Molex, myself.