If you are looking to rent, the windows and siding will probably get you better rents as they affect the curb appeal or the functionality of the home. 

As you can create multiple companies (and would really recommend doing so if you have different ownership structures) or use the class function (to track separate items for each property in one company file; though you do have to use a bit of caution and make sure that every transaction is coded to a class). 

If the repair is critical to the function/market value of the property, we're going in.

How is the functional use of the property (sleeping, living, eating) changing between the two groups?

My occupants have been solo female doctors on rotation and some solo female interns.

@Noelle Pritchard BarkleyStep 1: use the BP search function to search the millions of threads that ask this exact same question Step 2: Realize the BP search function isn’t the best so switch to google and repeat step 1.Step 3: Realize this question is highly dependent on goals, risk tolerances etc Step 4: Profit

I recently found a HELOC widget on Chase.com that makes it super easy for Chase account holders to apply for a HELOC and it even has a function to allow HELOCs to be converted into fixed rate loans after being generated. 

@Eric OszczypalaStep 1: use the BP search function to find the other million threads that ask this same question Step 2: realize BP search function isn’t the best so switch to googleStep 3: realize this question is incredibly personal and dependent on risk tolerance and goals etc Step 4: profit

Need about $3-5K in repairs, and is now functionally smoothly (and is up to code!)

The tagging function isn't working for me, but there is @Jason Ridout who has places in Port Alberni and Parksville, @Kris Bucci on the south end of the island,  @Jason D Lewis up in Courtenay and @Randy Molland who is either in Nanaimo or Victoria.