We are struggling with whether or not we should purchase a multi-family property and live in one unit and rent out the other or purchase a fixer upper for around $20,000, fix it up, and resell it.

I live in the basement because usually the basement level is the "lesser" of the two levels so you can maximize the rental income of the property by renting out the "nicer" level for more money.You are also right that walling of the upstairs and the downstairs can be tricky, but some front entrances are set up in a way where the stairs to go downstairs are right there when you walk in the front door, so you put up some walls that you will take down when you go to resell it as a single family home and create a little foyer and then you have separate entrances.

To offer some insight, I've been the commanding officer in a few different organizations, and dealt with debt collectors in various molds on a regular basis (probably once a week). 

  $800 excavator and operator, $400 oil "disposal" (likely involving them reselling at a profit). 

Also set your keyword alerts to pick up phrases that might also pick up posts from people organizing meetups near you.

IE your going to buy them for the purpose of reselling to  the public.. by doing any amount of work on themcall the CCB they are nice there they will tell you what you need.. or you can get a GC license then you don't need the developers license and you need the developers license for the entity that takes title ..

I'm going to cold call 100+ landlords in the area and organize an informal meet-up at the local tavern so I can meet a couple dozen landlords and let them know I'm looking to buy some multifamily properties..The downside of this idea is having to syndicate the money between what I can put down and what the local bank will finance.

Legally, you would have to purchase the property for the mortgage balance and resell it to the ultimate buyer. 

@Brian Burke  I think one main difference is the syndicator can send out a blast email to all investors at once on a specific property. turn key or PM has 1000 different properties for 700 different people and 600 different messages much much tougher..But generally speaking syndication is a higher level organization for sure.. 

My last personal residence was 5 bedrooms, but when it came time to resell it gave me no advantage.