Do you understand small towns ?
Population 259 small enough for you?  Or is that too small for you?  I understand small town USA.  Even in small towns people understand math.  As a business owner, when I pay two employees to spend a day cleaning up equipment and positioning them down in the city park and then spend another day bringing them back to the dealership and cleaning all the fingerprints off the windows and the clean garbage out of the cabs that go left their by people climbing over the equipment at the show.  I now have 32 hours of labor invested in making your show better by having new equipment on display and then you tell me I can only do that for you if I give you $500 after I just agreed to pay two members of the community to do nothing to make the dealership money for 2 whole days so you could have a display in the festival.

I have had the discussion with a few guys in my community about doning such and such fundraisers and how we would be better off getting second jobs and taking the money from those jobs and donating it in place of the fundraiser; we would all spend about 1/4 the time in generating the fundrasier dollars.  Take most any fundraiser and divide the profits out amongst the hours put into the fundraiser and most of the time it works out to under $2-3/hr.  Fundraisers are noble, but often very inefficient means of generating money.  Go back to the example of the dealer that will bring a couple million dollars in equipment down to your tractor show and then absorb 5-7000 in shop labor to contribute to your show and wonder why your demand of $500 for the privelage of doing so is not granted.  Now do that for all 4 communities that buy from said dealer and that is $20-30,000/yr that had to come from somewhere (they need to make it up from sales which does not help keep prices favorable.)  It has nothing to do with small town vs corporate America rather it is about appreciating the effort.  In our small town we would ask if they would like to contribute to the prizes for the tractor show, but no way would we demand they pay us to show up.

We expect them to support the community that has kept their doors open in hard times. Smaller stores certainly helped us, so could they have .
One hand washes the other, it used to be true.
I have been asked by my customers why we were not at such and such event.  When I explain that said event wants a $1000+ vendor fee, most of my customers comment "how would you make any money" to which I reply "The event suggested I rates my rates 25-50% during their event just to cover their fee and that I refused to do that, which means I would not make any money, so I stayed home."  Every customer fully appreciated me not exploiting them by inflating my rates.  Years ago everyone understood asking businesses to bend over backwards to make $%!& happen cost the business money appreciated anything they could do and if it was not feasible that was okay; today the attitude is the business does not care because they want to remain in business.  Business that go broke are no good to the community.

It still falls back to asking the correct question of "How will this make my event better?" vs  "What's in it for me?"

FWIW the event that wanted $1000+ invited us to their event this year because their attendees wanted us there and we negotiated a more realistic vendor fee for the event.  I have been on both sides of these conversations and it is obvious you have not.