- If you want to only make money the method your Dad has in the market he has then probably listen to him, otherwise don'tI think it is important to ask what's your goal with investing and what is your time frame, and also, ask is playing the waiting game in the family business worth the downside of not getting started straight away, paving your own way for success in a different market, and  having to deal with family regularly.I personally would strongly consider taking your savings, moving away from your Dad and to a market where you can stretch your dollar the furthest.

Summertime Chi is the best city in the country (if not the world), but winters are brutal and the south and west sides have stretches of blight, violence and a lack of hope. 

I would also like to know of any companies/ individuals who i could borrow funds to do the rehab on a rental property and stretch the payments out.

However, on a fixed income, I've stretched my requirements and have had good results. 

Make sure you don't stretch yourself too thin and you have money for repairs.

Id recommend trying to stretch the budget to $100k and look in Hazle Crest, Chicago Heights, Glenwood, Thorton, or South Holland where you can find 3+ bedroom that only need cosmetic updates but can still rent for $1500+/mo

Of course realistic but stretch goals are the best not some pie in the sky goal.   

I even had this bank lending me over 5 million dollars to do hard money loans in the deep south... ( which was a stretch for a community bank)..

A lot of people are stretched to the max as is, with rising costs they will begin defaulting on more mortgages creating more foreclosures.

I don't see this as low hanging fruit at all, would definitely be a stretch.