My other concern is that I get a place fixed up, only to have to wait until spring to get it rented out, which leaves the property vacant and a target for vandalism or squatting.Apologies for any ignorant stereotyping of the Midwest.  

For the most part after reading quite a bit of forum post, listening to Podcasts, reading blog post, and a few articles I'm familiar with the process.

@Christopher FosterYou may consider going to wholesalers but keep in mind competition is stiff as well and a non-refundable EM is required in most instances.

There was a litigation going on between the HOA and a builder in that community.

Take a look at some of the suggestions below:Check out the Start Here page http://www.biggerpockets.com/starthereCheck out BiggerPockets Ultimate Beginner's Guide - A fantastic free book that walks through many of the key topics of real estate investing.Check out the free BiggerPockets Podcast - A weekly podcast with interviews and a ton of great advice.

Afterwards we had drinks and a gentleman stated he would be putting his condo on the market soon.

Take a look at some of the suggestions below:Check out the Start Here page http://www.biggerpockets.com/starthereCheck out BiggerPockets Ultimate Beginner's Guide - A fantastic free book that walks through many of the key topics of real estate investing.Check out the free BiggerPockets Podcast - A weekly podcast with interviews and a ton of great advice.

I am not sure where you are at in the negotiations but I would offer a 6 month lease paid in full at signing at X - (large discount) a 3 month lease paid in full at signing at X - (smaller discount) and a month to month at X.

I puchased my own home about a year and a half ago and purchased a duplex in July that is currenty rented out.

I currently own and manage 30 rentals in our home town market.  Most single family with a few duplexes.  I'd like to start looking at a larger multi family building that supports property management.  Interested in to...