Our biggest challenge in the beginning was our on-site manager.

Laud area-Cash flow is minimal, $300 a month-Selling now would allow opening up of equity to redeploy in another market with over 2x the cash flow for a new build-New market won't appreciate as much as FL though (not even close)-Current home will likely get hit with higher taxes, insurance etc. in coming year and years to come-Biggest reason to consider just keeping current property?

My biggest piece of advice is to get a killer rental agreement/lease for Cook County.

I would look into them and try to figure out what their biggest roadblocks were.

I have three homes listed right now that have great revenue form STR.  

In anything, people are always the biggest variable, so it can happen to anyone, but adding in a variable of someone you don't really know exasperates that risk.If you just want "boots on the ground," hire a local property management company, and don't go with the cheapest option.

So I haven't officially started yet as we're out of state, but I'm thinking after I start driving for dollars and building a list to market to, the next biggest hurdle will be a buyer list, but from what I've been told, the right deal will draw the money.

What's the biggest value for your resident?

Many cities have high overhead costs that consume a large portion of generated revenue.

You are looking to create the biggest spread possible so shopping around for the best rate and terms should be a priority.