I've found that credit unions tend to look a little closer at your individual situation versus most banks that have strict guidelines you and your deal need to fit into.

The judge does thousands of these over their career or more so they have just about seen all the scams and excuses versus legitimate tenant claims.

I'm not sure the advantages/disadvantages of using cash versus financing are going to be any different here that most areas.  

Another risk of C4D versus getting a mortgage is that you need to ensure the seller pays the mortgage.

@PaulaPant over at Afford Anything has written a great blog post on the subject of short term rentals versus traditional long term rentals.

I would also keep in mind that title insurance is/can be/should be part of your exit strategy; it is a lot easier to sell a property wherein the buyer is comfortable there aren't any problems because you were already able to obtain insurance, versus having the potential buyer wonder "How come they didn't/couldn't get title insurance?"

Also, the way banks look at DTI versus portfolio lenders is different. 

Some build from scratch cheaper then they can buy.Alternatively you take a run down unit and fix up so your original all in investment is less so it raises your rent ratio.Example existing buildings stabilized are 1% rents or less but new construction or existing rehabs you can get 1.7% rents versus your all in cost.If none of that works your market might simply be overheated and you need to look at other asset classes within the area where there is value or change your strategy.

As some have already touched on, it is easier to get your degree while you're on the school track (versus going back after taking time off).  

There are LOTS of them on Meetup in my area (St Louis, MO) and I'd wager you'd have some luck on Meetup as well.