Answers

I agree with all of the above comments. The best is to start with the roof or where a leak is coing in from. Get that taken care of and then work on the foundation. 

Make sure you hire a licensed and insured roofing and foundation companies. Also ask about the warranties they offer. 

Do your roof first and stop water entry. As a general contractor we see these all the time. In almost all cases the foundation repair can be done at any point even if it means lifting the house and replacing the foundation. But water entry will continue to do damage if unchecked. So do your roof first. 

We agree with everyone that notes to fix your roof first, including any gutters and downspouts. Remember to be sure to run the water AWAY from the home. Water coming down around the drip zone of the foundation is a big problem and can be addressed with those initial steps. Then, you can and should address the foundation with a reputable foundation contractor. Water kills a home. Use the top down rationale and control it. But definitely fix that foundation but after everything above is corrected. Good luck.

Roof first, then foundation. (not saying that just because I'm a roofer :)
Gutters are likely involved too.

Fixing the foundation should not undo any efforts spent on the roof and gutters.

We suggest addressing your foundation issues first. Everything rests on your foundation. Even the slightest movement may affect everything above. Before you invest in a new roof, be sure your foundation is corrected.

Agreeing with most of the other comments here, we would suggest fixing the roof first to correct any water issues that may stem from it (i.e. ponding water near foundation, etc.) as well as gutter repair or install to run the water from the roof away from the foundation and home . In addition, its a good idea to look at the ground around the home to ensure that during rain or precipitation events, the ground runoff water is flowing away from the home or at least divert it away from the home if possible (i.e. adding drainage, etc.) before addressing the foundation. If you hire foundation professionals that take the time and care to properly raise the home and replace or repair foundation correctly, there should be no issues with the roof or any other aspects of the home. Hire a fully insured and licensed company always! Hope this helps!

This is really a tough situation because you have twice workload at your side but you nither able to decide the starting of your work. But you have to consider that if you start the roofing first then there is some possibility that when you want to start the foundation work then roof shouldn't get damaged so you have to start from foundation then Roofing. Because of first thing always first.

Now you know how you can get the work done properly and without any over budget issues. If you are still confused about then I can refer you a company which is really the professionals and provide you the best solutions for your work.

Fixing the roof first is crucial to prevent further damage. When addressing the foundation later, ensure the work doesn't affect the newly repaired roof. For roofing services, contact us at baystateroofingmasonry.com