All the work was done by friends and or family around 8 years ago when everyone was looking for work.

Dee Jay Chicago has quite a few issues and property tax increases seem to be one of their favorite ways to solve them.In a city like that I would also be afraid of regulatory hindrances like rent control and the city just not being landlord friendly in general.

I have friends that have property in a placed called Long Key Outdoor Resort.

I found some discounted REOs and the location through a friend, made a trip out there, and the numbers made sense.

In addition, I’d recommend going to real estate investment meetings in your area, making friends, and exchanging work for knowledge (or some similar arrangement) so that you can supercharge your skills without taking too much risk (see the BiggerPockets Events page, or google the topic).

Hi and Welcome to this big and friendly community.  

I've done as much due dillegence as possible on the property so far as looking at schools, crime stats, 'driving' the neighborhood in Google Earth etc.

Should I go to the realtor (which I am friends with) and try to negotiate a better price with the bank or offer my cousin the money to sign over the deed to me and bring the balloon payment ($25k) up to date, then renovate and sell.

 $200k total.Rent property for $1500  (net zero cash flow).High interest rates are your FRIEND now, instead of your enemy.  

Go to go the tax sales and make friends.