I have not had any trouble running the games on Windows 10, and you really only need to be able to run the latest version of the engine, as it allows playing the holds from older games. This way, here are even added optional challenges in all the holds that didn't use to have any, if those kinds of things interest you.
So, you can play all the other official DROD holds with the DROD:TSS engine. They should appear in it as downloadable content after you have purchased them and linked the games to your Caravel account. It's been a while since I did this, so if you want more info, just ask, and I'm sure someone will outline the exact steps to do this; and how it works on Steam if you'd prefer to have the games on Steam too.
Important note: This thread contains an announcement that you cannot link games bought in other places to your Caravel account. You should consider buying directly from Caravel. Afterwards, f you so desire, you can request Steam or GOG keys from your Profile - Purchases tab to add the games to your Steam and/or GOG accounts.
http://forum.caravelgames.com/viewtopic.php?TopicID=41409
Also, if you have any questions about what people would recommend you to purchase next and where to pick up the series after your break, don't hesitate to ask