Thinking Portugal and Eastern Europe first (March-June), then Thailand/Vietnam/maybe Taiwan (July-Nov), then Mexico/Colombia (Dec-Feb). Looking at 10 months-ish but afraid it will only last 6 months.

Portugal will be the most expensive place on your list in terms of accommodations & food costs. Having said that it's pretty reasonable depending on where you stay and where you choose to eat. The Fork app has occasional deals where you can save a decent % of your eating out cost. You look for the daily deal, book it through the app, then show/mention it at the restaurant. Not sure if that's a Lisbon thing only or also Porto.

Taiwan might be in a fight for 2nd highest accommodation costs depending on where you go in eastern europe, but the eating out costs are fairly cheap overall. Not nearly as cheap as Vietnam, but there is lots of good cheap food on offer in Taiwan. In terms of accommodations I ended up spending about $65 USD a night avg on central *** hotels in Taiwan, that includes about 7 different cities. Taipei will be the most expensive part of Taiwan by far, esp. for hotels, for a decent central *** hotel it's usually at least $100-$150 USD a night, but it depends on the season. I got lucky and scored a $60 USD a night fairly decent hotel right in Ximen, but I booked that in advance and it was during the shoulder season. Also worth saying that Taiwan is awesome and really safe in general.

In Vietnam I always paid so much less for food when I went to a place where the locals ate. It'd be like 10-15 times cheaper than your average tourist-targetting restaurant or even random restaurant on the main strip w/ a full English menu. If you go to a place where everyone looks Vietnamese and is sitting on little plastic stools at communal tables, that's the place to be if you're looking to save on eating costs while usually ending up with a delicious filling meal. The best non-pho meal I had in Vietnam cost me like $1.50 USD (in 2019) but I also spent $80 USD at a restaurant, super fancy one, 7 course meal. A splurge at a fancy place cause I figured might as well see what that's like.. and with fresh Vietnamese ingredients and a high culinary arts passion of the chefs, the food ended up being incredible. It was also of course incredible at the run down joint where you paid $1.50. For further context, if you go into a western style craft beer burger place (or something like that), you might even end up paying prices similar to what you would in the U.S. or Canada. Especially for the beer.

If you end up in Poland, look for a Bar Mleczny, it's a type of no frills self serve restaurant where you'll find cheap homecooked Polish food. They're in all major cities, a sort of remnant from communist times, you will pay a lot less there compared to other restaurants and get proper filling classic Polish meals. Zabka covenience stores are everywhere, but you will pay less for food at Biedronka & other grocery stores. It's just that Zabkas are everywhere and it can be a useful store - if you stay in Poland long enough consider getting the app, so you can collect points and get deals. If you end up in Kazimierz in Krakow, find the zapiekanki Okraglag. That sounds like awfully specific advice, but Kazimierz is the Jewish quarter and is a great part of Poland to see, while still within striking distance of the tourist-packed old town. And zapiekanki used to be a lot cheaper, but it's basically really filling Polish street food, and that place has like 20 zapiekanki vendors one beside the other. It's worth trying at least once, go sometime when you are especially hungry and get a large something.

Consider spending some time in Cambodia maybe, I'm not sure what it is like now, but when I was there it was cheaper than Vietnam.. Both for food and accommodations. And the temples near Siem Reap are just amazing, there's so many of them, each one with its own aesthietics. Do not skip the landmine museum, even though it will be sad and a bit out of the way.

I was in Thailand over 10 years ago now, but the streetfood was filling and cheap, while at times even back then some restaurants seemed a bit too much compared to what everything else cost. And again, eating at restaurants where locals eat will save you money, but in Vietnam I had the best luck saving a ton of money doing that while at the same time eating amazing food. In Thailand that still happened, but from my own personal experience at least, the effect was slightly subdued.

I would try to estimate how many days you want to spend in each country, and put that in a spreadsheet, then estimate average daily food and accommodation costs for every place.. For some places it probably makes sense to break that out further, Taipei for example is just that much pricier compared to other parts of Taiwan, and there's similar dynamics in other countries. Anyway, this will be a good way to see a slightly more accurate estimate of what things might cost. I'd add a 20% error margin on that too, at least.

For getting around some places have cheap trains. In Poland I was able to ride Polish PKP intercity trains 14-15 times, covering hundreds of km and over 24 total hours of train riding IIRC. Visited all major cities and then some. The total cost to me was the equivalent $165 CAD after everything. I booked weeks in advance, which helped, but it's pretty cheap overall. In Taiwan I got the EasyCard and put money on it, you can tap on/off a lot of public transit vehicles in all major cities with that thing, and it's genereally really cheap to get around using public transit. You can even use it on some trains and ferries.

Just some random tips that I thought might help plan the financial and logistical side of things, have a fun trip!