I read RDPD in two days so I'm going to need some more book recs ASAP as I'm fully submerging myself into this! 

Document the heck out of everything.CapExHow you chose managementHow you chose the propertyYour thoughts about the property going inHow you furnished the placeHow much it would've made long termHow much its making as a STR after stabilizedThe laws that state what your doing is alright... because,You're going to need at least 10% to do your next deal (unless you happen to move and free up your FHA again...) but probably more because 2nd home lending is very difficult now...  

Good luck with that--you are going to need it. 

Using the $50K value you cited, you are at around $280K with no surprises or additional carrying costs leaving you about $20K profit assuming you get the $300K sales price and you are not surprised with the need to add a new HVAC unit or something else costly . . . . and being a distance from where you live, you are going to need a GC to oversee the project. 

Once you are at the appointment or at least after you've met, you've already set the tone for future negotiations. 

I recommend putting all your profit in an account for emergency reserves, you are going to need it eventually.

I realize I am still under performing in reaching my first deal because I am still scared but have managed to muscle a little bit more courage.

Also, I agree with Brandon that B4 will build your "work your *** off" muscle.

Any good CPA can handle what you need. i don't see anything complex enough to need a tax lawyer yet. 

But I didn't feel I had the complexity yet to need Quickbooks.