We bought a Victorian home with some deferred maintenance issues about a year and a half ago, and the time has come to address some of them! The problem is, each item on my list seems to lead to another item, and I'm having trouble deciding where to start or stop and how best to hire people to do the work.

The most pressing issue, IMO, is the master bath. The shower is crumbling and badly in need of renovation. I could keep the current footprint, but the bathroom is extremely small (6'x6', maybe a couple of inches less) and I would really love to gain some extra room for a larger shower. The bath is adjacent to the master closet (also in need of renovation), so I could theoretically steal some space there, but there is also a non-functional chimney stack (on an exterior wall) taking up a chunk of what could be useful bathroom space, so we are considering having it removed.

We are having someone come out to give us an estimate for the chimney removal, but that opens up a whole new can of worms. If we remove the chimney, we'd have to have the roof and exterior wall of the house repaired. Our house is stucco, and there are some cracks elsewhere that we want to repair, so perhaps this would be the time to get it ALL done. But then the house will need to be repainted, which means the porch needs to be repainted as well. However, the porch is in need of some repair and replacement of improper footings, so we'd want to do that before we bother painting. And so on, and so on, and so on!

In addition to all of this, there are some other external projects we need to address soon (our outdoor wood and cement stairs need work, some of our retaining walls should be repointed, etc.). I know that I could simply hire specialists to do each of these smaller projects, but given the quantity of smaller projects and the interconnectedness of the chimney/bath/stucco/porch stuff, I'm wondering if we might be better off hiring a GC to manage all of it. Thoughts?

Obviously, deciding whether the chimney removal is worth the cost is a big part of this, and I will report back as soon as I get my first estimate. However, I would love some input on the bathroom and closet layout in general, because I really don't know if the chimney stack space is useful no matter what the cost. Here's the bathroom floorplan, so you can see what I'm working with.

And the rest of the second floor, so you can see how the bath fits in (it's the one on the right side of the drawing below). I am open to stealing space from the master closet or the bedroom behind the toilet, although I think the wall between bath and guest bedroom may be load bearing.

Thanks in advance for your advice!