My husband and I bought his childhood home with the intention of repairing and remodeling it. It’s been 16 years and finally we see an end in site. It has been extremely rewarding to to do this on our own. One thing we had to hire out though and could not wait was Roof Repair. We went with an insured contractor and they were done fairly quickly. Unless you have tackled this job before I highly suggest a professional for Roof Repair.
Our next major project was Replacement Windows. Replacement Windows are difficult to install and level. We were able to approach this task with a reasonable amount of patience. It takes 2 people and can be done on your own. If you have the funds for your sanity I suggest hiring a competent contractor.
Last year we replaced our siding on the barn with vinyl siding. Of all of the home improvement tasks we have had to learn and work on together vinyl siding is the easiest. We had an assembly line set up for cutting, hading them down to dad and even someone carefully measuring. Having accomplished these as a family is the best feeling.