I've been reading everything I can and analyzing deals as soon as something catches my eye, but the only areas around the chicagoland region that make sense with our crazy high taxes for buy and hold seems to be Aurora/Joliet.

Cost of cleaning between tenants depends on the region you are in, size and condition of the property.

After college I worked as a construction estimator for a high-rise developer in Toronto, and currently VP of a civil general contractor in Sarnia, ON.We cashed out of the city life a number of years ago and split the proceeds to by our own home and our first rental property. 

Myers, Florida region to help me make my first move.I am looking at condos within the $10ok range.My intent is to do a buy and hold with a 15% COC return and 10% equity, minimum.If there is anyone out there who is willing to help me out I will be looking forward to our conversation.Thanks in advance!

Check with your local/regional banks.

Contact the county or local planning department to see if there are any issues with building on the property - bring donuts and make friends as these people will make or break you.If you are unsure of the borders of the property, then have the seller order a professional survey be done.If there is a Department of State Lands or similar in your region then find out about any special delineations on the property.Find out about power.

I actually lived in downtown LA before I went to TX, so I'm vaguely familiar with the SoCal region.

Big money I am sure to get where Sean is.. you would probably need to do it regional say MS TN AL GA and Carolina's to make it worth super sizing..

I used to use New Western for the Texas region, but they do not do business in Northern California.

Toronto, Ontario