But i'd be willing to bet that you'll miss something along the way that will either cost you money, give the seller a leg-up on negotiations, or cost you the deal.   

If you want to rent it out right away you would get 75% LTV and a higher rate.When you go to buy the second property, you may be able to buy a fixer upper with all cash and then refinance that one after you fix it up.This is pretty much what I did (minus inheriting the property) and I have 11 rental units now.One thing to be aware of is your debt to income ratio in order to qualify for mortgages. 

We are looking at a fixer upper house to finance via a hardmoney loan for purchase and construction and then refi to a long term rental property loan.

The upper unit needs a kitchen remodel, but other than that it's a very solid first property I believe. 

On that wall backing to the basement steps, it looks to be about 5-6 feet, I would add either lower and upper cabinetry for dishes and small appliances or a large reach in pantry maybe both if the wall is longer than 6ft.Doing this will give you a really nice big "L" kitchen plus a pantry and washer/dryer off the kitchen.

This is on a basic mortgage not any 203k or fixer upper program, actually a piggyback mortgage(80-10-10). 

Basic assumptions ...Fixer upper houses start at 75k in your market.Fixed houses go for 150-200k in your market.You are bankable and can Rent, Flip it wholesale..

In your opinion does this seem like too much leg work for a small deal or is this a great opportunity to learn a lot on my first deal?

I don't have the time to go out and work the streets like I used to, so willing to pay a wholesaler to do the leg work of course. 

I had to click and find out "getting tased" was relevant to multifamily real estate investingIn all seriousness, you have a leg up on all of us.