Hello Mark, My apology for the delay in responding, but it seemed a requirement to know a little about Bayfield County prior to offering up past experience that might be on point. You manage a county that is four times the geographic size of the county I have managed (you oversee 2,000 square miles- to my relatively small county of 500 sq miles). With 25 towns, two cities and one village and a total population of 15,000+, the necessity of collaboration can be different than areas with a much more dense population. Also, your last unemployment data indicated a relative high number, about 9%. That can make a difference as to what works.
Both in the county and in cities and towns allowing the public to have 'skin-in-the-game' had a positive impact on public participation. It also tended to make proposals more serious, since there was ownership from the start.
We generally called these 'challenge grants' from the county/ city; and while there was a general guideline for them they were decided on a case-by-case basis. (and they had caps).
In cases where residents did not have the financial ability to match with cash, there was an allowance for 'in-kind' services. That opened up the program to all groups, regardless of income.
Our Corporation Counsel reviewed any necessary documents to limit the liability of the County/ City in such matters. For example, if a neighborhood wanted to clear and maintain a patch of land in their immediate area; we would consider the same so long as there was no adverse impact on taxes going forward. (eg. the neighborhood would also need to agree to maintain the area going forward, and indemnify the government )
You live in a part of the country that has scenic places to spare, so there may be a synergy with your tourism department in teaming up on such things. And with the published stories on a shortage of potable water; you have a state name taken from that very abundant and important resource.
Good luck. If you are headed to Boston, give us a call.