I absolutely hate my job and it is pretty much a dead end job as well.

If you used your investment money to pay the $36,000 you will have the entire cashflow of $500 per month for 60 months = $30,000, but if you get the loan you will be paying out  $230 per month extra for 60 months =  $13,800 extra, or a total $730 x 60 months = $43,800.For 8%, I would play it safe, keep my cash tucked away since it is very difficult to work and save $36,000 in one wad of cash and use someone else's money for such a low rate.

@Jay Hinrichs this case is different we know the owner is dead for the last 3 years.

I am sorry, but can we not play mind games and rather talk about actual experiences of people who have proven strategies in the market that we are in?

Due to the unique offering of the lake access in proximity to Rudolph Music Center, Grand park and the fact it has access to Morris reservoir I’m interested to get peoples opinion on What do you think would be the better play.   

@Max Langlois - smart play.

The amenities, pictures, descriptions, reviews, all play a part in how much you can charge.

Also seller financing is likley a good play here. 

Also not interested in the entity whom I won't mention who sold me an investment from here a while back with a dead beat tenant and shoddy rehab work, and a clueless property manager. 

I also want to connect with people in my area as well as others, to learn and possibly partner with In the future.Fun fact I play in paintball tournaments (speed ball) almost every weekend.