This girl spoke good English or passable, she wants to speak better, contrary to any crap you read, the Estonia normal blue collar worker does not speak good English. It is totally random however your Hostel manager may speak pretty good. Outside the cities it is terrible, however as always, sign language works.
I suspect your idea to buy a van to keep the travelling costs down is bit overoptimistic. In most of European countries you have buy rather expensive car-insurance. The cost of gas is also much higher compared to US (Estonia and Latvia have quite low gas prices compared to other European counries). In Eastern Europe you may want to try trains, which, as far as I know, are cheaper than buses. Also, I think it is much easier to find english speakers among young people - elders mainly speak russian as their second language.
Car insurance first quote is about about 149 per month.
The train is DOUBLE the cost of the bus, for sure anywhere in Europe the bus is cheaper.
I am calculating presently in Eastern Europe and for sure I can easily drive and save money in Western Europe. There is a braindead, non-thinking trolley tourist mentality that is not a budget or Shoestring traveler, in fact the Lonely Planet seems to have totally forgotten the path, they do not even give advice on how to live cheap, only how to party.
I am referring to a Lonely Planet comment on the English, it said all people in Estonia are Fluent, this has to take the award for the most inaccurate comment I have ever read in Lonely Planet. NOW... before any of you get the idea that I do not use or like Lonely Planet understand I carry it and it saves me money.
I think the biggest hindrance for me on cheap traveling is my 37 kilo bag and listening to anybody tell me how to travel. Obviosly all the travelers do not care to travel economically. This is there three month party tour and they are not travelers. The Lonely Planet should realize they are opening up themselves to great competition if they do not cover their bases.
I am 95 percent sure a van is the best way to travel Europe for the cultural traveler that wished to see the country and get off the Hostelworld.com reservation path.