27%! That's very little...
Providence, RI began a program called 'Trees 2020', which Many trees have been planted as a result. The number of trees successfully established will never be 100%, for sure, but the fact is that trees, even in relatively poor condition, still contribute to the goal.
It's difficult to stroll down some of the sidewalks due to low branched nursery stock, but that;s a small price to pay for so many trees, IMO.
RIDEM has also issued a statement to all RI licensed arborists which demands any tree over 28" DBH (correct me if I'm wrong) must be approved prior to removal. I think that's a step in the right direction, for a city. I'm sure large trees are still being removed without permit, and I'm sure there will still be situations in which one hand will wash the other to get healthy, valuable trees removed, but still...
Maybe you can start an new iTree inventory and create your own register of valuable trees. That's something I'll be aiming to introduce in my town, and a nearby park, over the next few years.
If you're looking for funding, you'll need to have a committee built to oversee the use of the funds, and an inventory will sure help to show that you're serious.