He is not comfortable finding a tenant on a timely basis. 

You definitely need to be in MLS, whether you use a full service agent or a flat-fee broker depends on how comfortable you are with the process of a real estate transaction.

Not saying its for everyone, but take comfort in the fact that everyone who now owns investment properties once had no experience. 

Hey Alexander,I've worked with Yen Design for architects before and had a great experience.I might have some of those other resources through my network.

A family with young children is unlikely to be comfortable having a stranger living in their backyard. 3.)

I live and invest in a classic "cash flow markets" (which has seen 8 years of steady appreciation and is hyper competitive and has very little inventory), and I would not feel comfortable to promise you quick and easy cash flow, certainly not within the time limitations of a 1031. 

I would suggest to start researching Idealista, however even before that thinking yourself where you feel comfortable to invest and what your investment plan would be.

I would put the student loan on an automatic minimum payment plus some comfortable, but not too large, additional principal payment (if available) per month, then forget about it.

I'm from Italy and I will relocate to Missouri next year: considering my background in architecture and design, I would like to start flipping houses with a focus on small, old properties to rehab (just because my european concept of space may help when it comes to optimise small houses).

look at your experience level with reality in mind.I would want to feel very comfortable about those things before spending time on deals and money when i had no real capacity to transact no matter who the lender was.