We typically take out cash flow 1X per year close to the end of the year based on what is left in the operating account and our thoughts on proposed work to the property the following year.

Talk with your lender about this proposal...  1) Get a solid quote on the roof replacement and share it with your lender.    2) Put the funds in escrow with your bank for the sole purpose of replacing the roof.    3) Close on the property.    4) Install the roof.    5) Get reimbursed for roof expense out of escrow.Most banks are fine with something like this if they know their downside is covered.  

I go through all my parts obtaining private funding, getting contractors set up (meeting dozens of them to find the right ones), and I’m about to get my civil engineers plans for the addition as well to propose to the town the day after closing.

If you’d like advice on how to approach private lenders or need help structuring proposals, feel free to reach out!

I had also seen a year or so ago that the community wanted to put more restrictions and require a local contact, and limit on number of permits , but haven't seen anything more stringent since that proposal failed.If you can share your experience, I'd greatly appreciate it!

On my agenda I plan to meet with my realtor, a couple of proposed property managers, and visit a couple dozen potential listings.

Think about it as dating... you want to be prepared to propose but don't want to take the ring out of your pocket too soon! 

As example, to cover how much of the proposed rental income from departing will be credited against those mortgage payments.

Hire a Architect to provide drawings with a lot of details such as existing house elevations and floor plan, proposed elevations and new floor plan, roof, wood deck, addition, etc.

In your proposed situation, here is what I would do:1) Make sure you have a good/solid/reliable contractor that can actually do the work and has capacity to handle the project.2) Apply for the max HELOC and get it established.