Told him to check the references at the downstairs coffee shop for verification, he thanked me and assured me that in their hometown in Missouri, it was a dangerous city, thus the concern.....I have no clue what they do in Missouri and I can't imagine it's what he thinks it is but it sure made me aware of how visiting an unknown place causes certain anxieties in people, mostly unfound but not always.   

I would first of all tell you to read Gordon Moss book Performance Anxiety which you can find on Amazon.

My hesitation is two-fold: 1, I fear just royally messing something up with the paperwork, but that's just regular nerves about trying something new for the first time and I'm sure doing my homework would help with that fear. 2, I am wrapping up a master's degree right now and the thought of doing more school is giving me some anxiety.

But keep in mind that flipping is a "job" and you need to convert that cash into recurring passive income.Now, how do you scale in a high priced-market?

Also, I was trying to get 80% LTV on this deal (because it supports it) and the local guys have been pushing down their LTVs for this market.I think that the biggest anxiety most people have is the whole liability, asset protection, and anonymity thing.

It gave me a little anxiety that he and I would not see eye to eye on how to run business.  

My bank gives free checking accounts to individuals but charges hefty recurring fees for a business account.  

I guess if you can speak to crowds and not have the anxiety to do it then it can be a great way for sales people to make fast cash. 

It may seem a bit excessive at first, but the money you spend with one around tax time will be well worth not dealing with the headaches.Find sources of cash that are recurring and make sense.  

I recommend some more formal business oriented options below:cozy.co - website with no fee rent collection service- no fees for either party. newer entrant but seems trustworthy and user friendly. haven't used this yet.https://www.biggerpockets.com/forums/92/topics/198046-cozyco-reviewshttps://ipn.intuit.com/ - Intuit payment network- 50 cent fee per transaction and can be recurring payment. reputable company and relatively easy to setup.