It is very hard to find something legit in this space due to the overwhelming amount of spam and scams geared towards what I am looking for.

I personally think anyone who doesn't put down 10% or more is gambling, but you probably think I'm an idiot, doubly so if you are still reading this...Jeez.  

It could appreciate but I consider that gambling.

I literally won't work with these guys because all I've seen from them is daisy chain deals.Now, when I see deals from them (still can't manage to get their emails to go to spam 100% of the time), even if I can't find out for certain whether it's a daisy chain, I won't even consider working with them because I don't feel like they're trustworthy.Being transparent and honest will get your far in this space, largely because it's so rare.

Garrett Gamble I do have a couple that I’ve personally used.

Well it sounds like your ads are being seen as spam.  

I do post them in many categories, seems spam-ish, but I try not not to flood each category.

But Action without knowledge is a gamble.  

So basically in a situation like this it is a gamble as to what the city will settle for.

Send his emails to spam.