I can get you a free guestpass if you like. 

Most certainly you can thrive in roller coaster if you are well informed and can make the right decision as to when you should buy and when you should sell your RE, just like any other commodity on the market.   

The most important factors a hard money lender will look at, if you don't have experience, is your liquidity and credit score & history (as well as your background -- no liens, judgements, foreclosures, bankruptcies, etc).I would hit up @Michael Cid -- he's a tremendous resource and is a direct lender. 

Like LLC, S-Corp, C-Corp, etc.

What I have found is that like cabins, one with a view and the other with a pool, that the pool cabin will significantly outperform the view cabin, all other things being equal.

Your success is much more influenced by how well you play in a market, how good your team is, than by picking a marginal better market.

Sounds like the seller may not even have file plans or obtain any variances.

I personally like the Midwest for its affordability and cash flow potential.

To that end, I would find your local REIA meetups so you can also connect with your local market as well.  

At this point I have read the How to Invest in Real Estate - Ultimate Beginner's Guide to Getting Started and I am currently reading Buy, Rehab, Rent, Refinance, Repeat as well as learning what I can from the BiggerPockets website.