We got this from our agent:"The cities that are difficult to deal with list:Calumet CityCalumetDoltonBerwynMaywoodRiversideChicago Heightscity of North ChicagoStone Park"We started calling Cook County, "Crook County."

#2 City Fheps has started making payments well above what the tenants owe.

If you don’t, then at least start with an appraisal and go from there. $145k sounds like a good starting point to me. 

Ideally, you operate as close to break even (or slightly better) in a market that's strongly appreciating.

I'm new to the area, and thought that joining CT REIA might be a way to start out.

Where would you start with $5000

If you prefer to have the MMLLC involved from the start, consider a "drop and swap" strategy, where the property is moved into an LLC before the exchange, though this requires careful timing.

Yes it is a strong market for cash flow, low taxes and landlord friendly.

My family and I recently relocated to Orlando where we also started a Vacation Rental Property Management company. 

I have been trying to get started in investing in RE in Canada.