I'm in the second batch and am in Chile right now.
The required events are not that time consuming. The reimbursement process will always take longer then you would like but it is not that burdensome. Also other Startup Chileans can help you out with the process if you need it. As for the other requirements they are not that time consuming at all. In particular if you are in a team you can divide up events as not the whole team has to go to everything.
Compared to Canada I find Chile and we can get by easily with the maximum salary. That being said finding housing as each successive round takes up the already limited supply of furnished 2-3 bedroom apartments.
As for local talents, I have not personally had to look for any but from what i've heard finding talent with good english skills is quiet difficult
In terms of social isolation, and cultural issues, I would say one of the advantages of the program is that there is an instant, English speaking, community for each round, so everyone has an instant social network. That being said, I personally find it frustrating that my lack of spanish skills mean my social network is limited to the program, as I would like to connect more with chileans and chilean culture.
The biggest culture shock for me was the lack of trust. Coming from Canada, I didn't know what to expect by the term 'chile is a low trust country'. It means security guards everywhere, it means retail processes are more complicated (buying an electronic product involves 3-4 different stations you have to go to) and it means nothing happens unless there is a contract.
Overall I find Chile a wonderful place with incredibly friendly people (and very patient when you butcher their language).
I'm Rimbo's teammate, I'll pitch in my two cents. mercadolibre.cl is your goto classified site, however most people in the program don't use it. There's also olx.cl. For housing homechile.cl is pretty good.
We arranged an apartment through homechile.cl before we got down. Honestly I would only recommend that if you've never really travelled before as the place we ended up getting isn't really the nicest. Most people come down and stay at someone else's place, their padrino's (a local arranged to be your goto person) place, or hotel/hostel it for a while. I'd recommend to take your time once you get here finding a place to stay as there are some amazing apartments that you may miss out on if you search online.
I am going to note that you should come down with at least 10k in your pocket. The first reimbursement is very slow, it usually takes about a month and a half to two months. This is because you first need to get your RUT card (identity card, you use it for everything), then have the program prepare the contract, then sign the contract, then wait for their lawyers to sign it. After that (about 3 weeks) you are officially in the program. For our round we could expense things up to this point however a round 3 wave 2 participant told me that they could NOT expense anything until this point as a rule change. This means all those expenses are out of pocket. The reimbursement phase takes about 2-3 weeks and you will NOT get all of your expenses approved the first time you submit. As an example, we only got about 52% approval. There's a lot of little things you need to do for every expense and it's really hard to keep track of them all.