Well, it looks like we will most likely be heading back to the family farm in a few weeks to stay, and I am in the process of drawing up a list of projects that I will have to start on. Due to budget (on the low side), almost of the work is going to be DIY so I will probably become a fixture in this thread looking for advice.
The most serious issues are not ones we are going to do ourselves. The first is a new furnace (so obviously not a DIY project) - my father-in-law had the very nice one installed about 10 years ago, and has hardly been used, but it was installed in a cellar with no moisture protection resulting in heavy corrosion in the electronic controls. We are planning to have it checked to see if it can be repaired, but budgeting for replacement. We spent the winter 2012 there, and it was bad with no heat (or modern insulation - 160 year old house).
The second main issue is the roof. One, I am not going up on that roof without a cherry-picker and safety gear (see picture below), and two it is metal. This is something we know we will have to get the entire family to chip in on since the last quote anyone got was $25K not including any repairs to the actual roof structure. We are also looking at metal roof alternatives like what was used when the family replaced the roof on the carriage house/smoke house (I drew a blank on the material name).
The first planned project is cleaning off the old latex paint that was used awhile ago and now is coming off in strips. Also, at some point in the past a milk-wash was used (we think about 30 years ago). What would folks recommend for primer and paint types - oil primer/oil paint, oil primer and latex, or should latex for both be ok as long as I am make sure the primer is put on correctly? I have tried to find information on ye' ole web but it is the milk-wash that seems to be a stumbling point (most discuss new plaster walls).