So i started down a path of reading and investigating success and happiness material and have been very pleased with my progress in that realm.  

Roof first if it is near the end of its useful life.Siding I would also look at for weatherproofing (wind driven rain could also rot your building).Once it is water tight, I would start on any code issues (see inspector mention), then maybe on to kitchen. 

Also, any material of potential flyers, mailings, etc. 

Go through those materials and then you can ask more specific questions.

There are the big box stores (HD, Lowes, Floor & Decor) where you will find middle of the road materials at middle of the road prices, then there are the higher end producers (Sugatsune, Andersen, Geberit) that you buy direct from the manufacturer.

Budget can be $10-20/hr plus materials. 

He charged $350-400 on an average window, labor and materials included.

I'm very ambitious and driven just wish I could have started at a younger age. 

Depends on the quality sometimes cheap materials are used and can have foundation settling issues, also difficult to find the builder for warranty fixes.

You need to prove material participation.