I did go to the tax assessment page which gave the house a D grade and condition of average.

@Robert Davis IIIOut of state is a great thing, if you live in California :-)It is defiantly doable, I know many people who have their entire RE portfolio out of state or out of country...Now , with all that said , if this is your first RE investment then for sure you have to visit the area, and get the local insight, plan your trip ahead and have everything lined up:Several "potential" properties that you would consider investing in, tour them real good and grade them for yourself ..When you visit these subject properties make sure to blend in as much as possible with locals , neighbors, mail man and everyone in town that will be happy to discuss and contribute REAL local insight ... at this point I would not take advice from anyone that is talking from position...

I have an acre lot that needs to have drainage and grading plans drawn up before I can start designing the house.

Unfortunately, I believe this is, above my (pay grade and) expertise.

Turnover, vacancy, grade of improvement required, and time to refill all increase dramatically in some of these out of state markets where there are more rentals than tenants.

Practicing Pharmacy can be rewarding in its own way but i need more freedom and i see this avenue as the ticket.

Is house hacking A Grade properties a bad idea (as long as the numbers work). 

(ours is up 3 miles of steep grade pavement and then another mile of gravel... but the view is to die for)I would urge you to be especially conservative with your vacancy rate - Maggie is pretty much dead all through the winter, and over the years I've seen many, many small businesses come and go because they couldn't make it through the low season.  3-4 months of little/no business is the entirety of your 33% vacancy. 

@John Clark......my tenant grade is E5 This is what is stated on his Defense Finance & Accting Service Millitary Leave and Earning Statement

If i am sure that I will go the Rent strategy, I would spend a bit more to put in more durable finishes such as tile flooring potentially higher grade countertops and casework, etc, compared to flipping.