Hello Jimbo and welcome to the NS Community.

Great that you are planning to visit The Netherlands. The train is a nice way to travel around. You could consider one of our NS Flex subscriptions. For example you can take NS Flex Dal Voordeel, which gives you 40% discount on all trips during off-peak hours. All our subscriptions can be found on this page. Every subscription comes with an OV-chipcard, a travel pass that you check in and out with before and after your trip. NS Flex subscriptions may be changed or cancelled on any moment after the first month. 

We do also offer e-tickets and day trip tickets to visit touristic hotspots in our country. Enjoy your stay!

Getting an OV chipcard for the NS Flex subscription would be a challenge however, as @Jimbo states being Canadian. That would be an expensive overseas call to customer service and OV-chipkaart doesn't ship cards to Canada AFAIK.

Should TS know someone in the Netherlands, probably it's easiest to ask them to order the subscription for him and have the card sent to them as well.

Otherwise: maybe TSs hotel is willing to function as a postal adress for the chipcards?

For 4 weeks, the Dal Vrij card is your best option for a month's unlimited travel at a fixed low price. Indeed you will need to get personal cards made and delivered for this, so someone in NL will have to take the delivery for you. 

You can buy the Holland Travel Ticket as well from the machines in Amsterdam Central Station but it's quite expensive: 48 euro per day per person. It is valid for one day on all trains, buses, trams, subways in the country, and only valid at non-peak hours (after 9.00 am, at weekends and national holidays valid the whole day). The peak hour version is 70 euro.

Dal Vrij is much, much cheaper. But this not geared at tourists, because you need to have a personal OV-chipcard. As has been said: you can buy this but for purchasing it you have to work your way around by using someone's address in the Netherlands.

There is no special and reasonable priced tourist ov-travelcard that you can buy online for a fixed price and valid for (for example) 7, 12, 15 or 30 days in a row. Other countries in Europe do have this, but not the Netherlands (this would be quite an improvement for tourists using public transport and seeing all things our country has to offer. There are great things to see as well far beyond the Amsterdam area )

Difficult to answer.

You can travel in the Netherlands with your credit or debit card. With these passes you can check in and out at the public transport poles or gates. You travel at full fare.

NS has several subscriptions, such as off-peak, off-peak discount or weekend off. What is cheaper depends on how much and when you travel. These season tickets are only valid on the train, even then you must always check in and out. The time of check-in determines the rate.

When transferring between 2 carriers, you must first check out and then check in.

Sending abroad is difficult and perhaps impossible. Perhaps the most convenient solution is to send the OV chip card with subscription to the hotel (but ask the hotel first). You can travel to the hotel with your credit card.

You can also use the OV chip card for other public transport, such as the tram or metro. You will receive an invoice afterwards.

OV chip card is only valid in the Netherlands. 

This is a continuous subscription of at least 1 month. You must cancel the subscription. You can keep your OV chip card.

This is only possible in the Netherlands. Every country in Europe has its own ticket system.

If you are traveling across the border, it is best to book at least 3 months in advance. If you want to make decisions at the last minute, you can use Eurail.