Option 1: invest in multi family housing Pro- semi reliable income- cuts cost on my living expenditures -recession proof (can be argued)Cons- high cost start (for me at least)- first time managingOption 2: Buy land and try to negotiate a development deal Pro-huge reward -can be fast- after deal is done right, I'm hands offCon-very risky especially for intro-no expertise in this field -finding a great deal in hardOption 3: wholesalePro-great return-can be fast-not long term Con-hard to find good deals especially with a full time job -can be a nightmare project-no expertise Please correct me if I have messed up with any of my pros/cons.

It's that simple!

If you run a tight ship I think you can make it work as long as your local and hands on.

Both SFRs and Multi's can be great rentals.  5) Manage this second one yourself to see first hand the complexity, but then plan on hiring a property manager for #3 and #4 after you get tired of whiny tenants. 

Assuming this is a long term buy/hold investment, then this is a simple math exercise.

I've networked with an experienced flipper who found the deal and proposes I finance the job, he does most of the work and manages the subs and I take up the painting of the house and lend a hand with some labor. 50/50 split on the exit.  

I've narrowed down to a handful of areas, and on paper Fort Wayne seems like it's full of potential opportunities.

If so, this is a simple ROI calculation, and thus depends on how long you want to break even.

I am mostly just looking for a bare bones cheap simple build or manufactured home. 

Also note that taking over a mortgage for Fannie and Freddie loans are not as simple as people may think.