Hi, I live and recommend Barcelona, in Spain.
I've been in the games industry for +10 years, last 5 working as a gamedev teacher and also managing my own start-up, got daily contact with most of the studios in Barcelona (where my students do internships, I'm the coordinator) and I usually attend game-related events in Spain and I also give some conferences.
Gamedev community in Barcelona is very active (most of the devs share a Whassap group) and we have different regular meetings. Also, there are some big gamedev-related events (
Gamelab,
BGW,
MWC, ...) and gamedev business accelerators (
GameBCN,
BarcelonaActiva). A part of that, we have several companies developing their own technology and an active MSX dev community.
In addition, Barcelona is a beautiful city, weather is amazing and mediterranean food delicious. :)
About organizing a HandmadeCon, well, I've only organized some meetups and I'm not concerned of all the requirements to organize that kind of event, also, don't know the specs of the event... Getting a space for 200 attenders for a couple of days and offering some acreditations and goodies shouldn't be a problem, probably finding the speakers is more work and get fundings from promoters could also take some time. Personally, I can put some money but I don't know the general cost of the event.