Sorry I don’t have any advice about the roof; we’ve never had to replace one.

About the rest, if you haven’t already done so, I would hire a home inspector to thoroughly examine the house for problems.  And since it is an older house, I would seriously consider a structural engineer as well.  On the advice of a home inspector, we hired a structural engineer to check a house we had a contract on.  It cost us a few hundred dollars, but saved us thousands as we then decided not to buy the house because of several expensive-to-fix problems that were found.  I would include the home inspection as a contingency.  That way, if many problems come to light, you can cancel the contract without losing your deposit.

Good luck during this exciting (and stressful) time.

Since I don’t have much experience,  I would hire a home inspector, they know what to look for.  You may have already done this.  Some things that I remember checking for from my moves : Check the septic tank (if not on sewer , to see if full and works right).
Check for termites   Check for lead paint .  Check for water damage/mold from any known leaks.  Check if home has enough electrical outlets for all your needs and enough watts to run the house.  I’m sure there’s lots more, but thats all I can remember for now..good luck with your new adventure.

We just moved into a foreclosed as home as well - great deal!  I don’t know anything about Shaker Roofs but I definitely second the inspections.  The inspector we used brought an infrared camera to check for plumbing, etc. leaks that cannot be seen (behind walls, etc.).  The house we bought had a mold issue due to a downspout that was moved and all the roof water was dumping at one corner of the house - for a whole year!  We wanted to know the extent of the damage - it showed that nearly the entire floor of that room was moist underneath.  The inspector told us that most of his clients don’t have an issue they can see - but he does sometimes find things behind walls, etc.  So, I would highly recommend, with a leaky roof, that you have an infrared inspection done.  You might you have some one time - contained - damage that you could deal with. Or it could reveal a can of worms you may want to run from.  Good luck!  Buying a bank owned home can be a lot of work - but we are happy we did it!  (We close on our old home in a couple weeks - as we spend this weekend moving more stuff - I’ll offer up some of our work for your decision.)

I second the advice of a structural engineer. Our inspector told us he didn’t think anything was wrong with the foundation, but recommended that we get an expert to check it out. We cringed at spending the extra money and didn’t hire the engineer because the inspector hadn’t thought anything was wrong. Now we regret it. We had a friend who is a contractor tell us it probably would be about $30,000 to fix our house. We don’t have that kind of money and wish we hadn’t been so penny-pinching when we bought the house.

Don’t know anything about that kind of roof.  I *do* know, however, that your average home inspector can miss things. (I hope I’m not offending any home inspectors or their spouses today!) I suppose it’s like any profession; there are good ones & not so good ones. 
We are so happy that we joined AngiesList.com; we’ve saved well over the $40 membership fee in just a few well-researched repair visits from plumbers, etc., over the past year.  I’d highly recommend that you join up and find either a well-referenced inspector or engineer.  Good luck!

I would check with your insurance to find out if the type of roof makes a difference in premiums. You can also call roofers to get per unit estimates on the type of roof over the phone to help deterimne basic cost differences.

I second the idea that a home inspection is only as good as the home inspector.

Thanks everyone so much for your help, ideas and stories!

I have a couple of building inspectors that I am going to contact tomorrow, (Through Angies’ List—thanks for that fabulous idea)and a septic design company who drew up the plan for the septic that must be put in soon.

Thanks for the info about shake roofs, I remember helping my Mum and brother rip her old shingles off of my old childhood home, and I was struck with how brittle and flammable they seemed.
\ I haven’t found an engineer in our area, yet, but have a good friend who does remodeling and repairs and I hope to get his *eyes* over to the house to let us know what we’re up against with our bid…if it is to be God’s will, I hope this all works out!

You are awesome and so helpful!

Kat, thank you for this post!  It is exactly the kick in the pants I needed to just *start*, for goodness sake, instead of getting bogged down in the details.  Bins!  I can do bins!