My price range is usually 30-35K in neighborhoods like Oak Forest and Woodville but I don't expect them to be turn-key ready.

There is a local meetup in Lake forest every month that you should check out. http://meetu.ps/2QWCkhIf you would like to meet up before then and talk about investing let me know.

unless it was a recreational type property were my sole purpose of buying was to just recreate on it and I don't care when and if they ever get title.. or its ag or forest lands etc were titel does not disturb my ability to grow asparagus and then harvest and sell said asparagus

If im new in the business  i would probably invest min and have some money in the case i need to replace heater in middle of winter. 

My father has been a small residential investor in Toronto for over 15 years, and with his help I purchased my first property in downtown Toronto last winter. 

didn't check all windows and didn't bother on the furnace (it was in july and I replaced it in the winter as it was beyond cold in the home).so, it got me to thinking, what % are not to the level they should be?

Winter and road construction. 

There is also a parking ban in the winter from December to April that would pose a problem for winter 6 month leases.

These are all separate line items in the closing disclosure:Line item: INSURANCE Premium $2500 (will be go to insurance agent @ closing)Addt'l Line item: 12 months INSURANCE escrow $2500Addt'l Line item: 3 months INSURANCE escrow @ $208 / month, for a total of $624Line item: 12 months TAXES escrow $7000Addt'l Line Item: 3 TAXES months @ $582 / month, for total of $1750If you add all that up, they are seeking $14,375 in escrow for est $7000 in taxes (due in Nov) and $2500 in insurance due in 12 months.  

We are currently meeting at Vaughn Forest Church the 3rd Tuesday of each month.