But I know each year that passes will get us closer to where we want to be.

For smaller multi 5-10 many find DSCR loan to be the best in terms of ease of qualification while still keeping terms closer to what you see on a conventional loan (30 year term).

If on the other hand you do them to save money then maybe take a closer look at your options.

For Woodlawn- The closer you can get to the University of Chicago the better. 

Also, if searching for towns closer to you, I hear that Bethlehem, Allentown and Scranton are bouncing back after long declines but are still affordable.

@Sam BoothTrim trees (don't cut down), flowers or plants along walk way, paint door, river rock or some stone where bushes are, Dark mulch around tree, plant grass, drink a beer and call it a day.That said, I have no idea about the ARV in the neighborhood so that could be too much work...or too little.

Anything in Westover or closer to Raeford will be a great area for rentals including prices ranging from about $1,200-$1,800/mo. 

Much like fix and flip loans spiked up to 11-14% for a while, and are now back in the high 9's to 11's, I think it's encouraging to see the terms floating back to closer to where they were before. 

I was hoping to get 1900-2000 for my 3 bed, which is more or less the going rate, if I were just a few miles closer to downtown and/or had a kitchen with back splash/new floors.

The national average is closer to the 4-5% over time.