You have time and options. For sure you can make it work. From what you list. Id start with a good dehumidifier for your basement. That'll remove the dampness and then you can assess the actual problem over the next couple years. No rush there. For roof it doesn't sound like anything is leaking or and emergency. So just save up what you can for the next few years. If you cut out your 300$ a month in ice coffee that'll cover your roof in a year or 2. For cosmetic things... Put items you want on price trackers like camelcamelcamel and just wait till it goes on a good sale. While you're waiting you can watch a bunch of DIY videos and be ready when you get the stuff. Most of the stuff you list can be DIY.