Would it be best for me to come in as an investor/contractor as one business entity and her and her family come in as partner in a separate entity. 

Although each market is different, College towns are the same, especially smaller ones.

I have been told that it could be better to save the FHA loan for a later property (Possibly a personal one), if you can put 20% down for a standard 30-year fixed loan.

With a bit of planning and good operations, one can easily manage 20 to 30 properties without an assistant, with less than a day or two a month.There's lots of automated ways to check on rent, make deposits (my tenants deposit directly into a bank account), receive maintenance requests, have maintenance done, etc., etc.One thing I could argue is to have your tenants ONLY email you, especially for maintenance requests, and that email goes directly to the vendor that you have set up to handle it.

Jay I still have one of those books hanging around.

That one's on me. lol it is a lengthier post so I don't blame you!

With one deal under your belt, financing may also be easier this time.

Hey @Buck Dabill, it's difficult to say without the data, but we would assume if the property is on a lake (especially one used for fishing or summer activities) you could demand a higher nightly rate.

The only ones I could really find were Aspired and Allegany.

I am one of those investors