Manchester (New Hampshire)
I'm looking for somewhere to live not covered in snow, where I could live alright for a month or two on very little, but still have access to decent wifi for work and eat healthy. Maybe a cheap timeshare/other-share or an amazing hostel? Budget would be 600-800 dollars/month.
If Costa Rica wasn't so expensive I would recommend that. But it is so I'd go with Nicaragua. It's very similar to C.R. At half the price. You can easily find a place to rent for next to nothing and all the food is farm to fork in the less developed areas. Work a deal with a local hotel to get wifi work done with a beer. Tip well and you have free wifi !
I would defiantly recommend Chiang Mai Thailand surrounded by beautiful mountains and heaps of waterfalls around and this place is the hub of nomads. We are here for total of 2 months. Staring winter here in Chiang Mai but not very cold for us 30-34 degrees during the day nights are bit cooler which we find it nice and pleasant.
Wifi is available everywhere if you buy a AIS sim card which is only US$1.50 they have this co working place called C.A.M.P. AIS - Creative And Meeting Place in MAYA Lifestyle Shopping Center it's on corner of Nimmanhaemin and Huay Kaew Road,we find the internet very reliable.
Cost of living is really cheap here, you can rent an apartment for 1 or 2 months we pay US$7 a day for out studio apartment without kitchen, if you get one with kitchen the cost is bit high, most of the people don't have kitchens in their homes they all eat out as it works out cheaper to eat out than cooking at home. Heaps of healthy eating options are around we eat broccoli chicken with egg most days the cost is only US$1, heaps of gym's around I am at Hill side paying US$7.50 a week, we go to the whole sale fruit market each week we spend US$12 and come home with the following
10 Drinking coconut
1 Whole watermelon
kg Sweet mango's
kg Passion fruit
This week we found Avocados at US$1.2kg
Life here in Chiang Mai is great ! With your budget you will do fine here in:) Hope this helps you to make your decision happy travels :)
Mentioned in this answer:
I'd go with Costa Rica. Cheap cost of living, easy to get around, friendly. Great food, too! If I had to pick a specific location, I'd go with Monteverde.
or maybe Thailand. Cost of living is fairly cheap and you have free wifi at most of the places. All these places are close to each other so you also have the option of hopping to another place if it does not suit you. These places have good number of tourists and backpackers coming in from Europe and other places so would be good to get in touch with someone who is planning a similar type of trip. There are various groups on facebook and on web where you can find such groups.
Mentioned in this answer:
I'd recommend Thailand! Everything is cheap, warm weather, friendly people.
I'm going in 2 weeks for 2 months, also to escape winter;)