I would love to hear the thoughts in this group and what you would do in my situation and how you would strategize.

The experienced investors don't time anything; they strategically sell properties when the equity far out ways the rental income.

@Isaac Howell and @London Stewart my advice for beginners is to formulate an actual plan, road map so to speak, about the path you want to follow for investing.

Is it just a matter of strategizing (finding cheaper materials, wholesaling well etc.), or are my example numbers wayyyy off?

Frank gallineli book was excellent with detailed calculation on how to formulate cash flow.

I handle out of state clients very strategically, set you up on a drip or send you a few properties, you tell me yes or move forward.

Been lurking for a while as I learn and formulate some strategies.

This could be formulating a price that works for you and hand picking comps to justify it. 

How much you can borrow is based on the net before debt cashflow the project generates which a lender will use to formulate the amount it will let you borrow which is generally determined by applying a debt service coverage ratio which varies for different deal types which I believe is ~1.40 for a self storage property.The equity you put in will receive the balance of cashflow after debt service which forms the basis of your financial performance (cash on cash and IRR upon sale on a pre and post tax basis).So, the amount you can pay to acquire the property and cover deferred maintenance is equal to a price that allows you to generate enough cashflow to cover debt service and provide you with what you consider to be a reasonable return on your equity investment.HOW you pay is highly related to WHAT you pay.

Zillow and Trulia are not worthless if you do it strategically.