EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

This dually provides evidence and reassurance to the buyer of hard anticipated costs and a written estimate to support and help validate the buyers request to the sellers. 

Is it feasible to obtain a loan or a good old boy agreement where a lender offers 100% financing for both the purchase price and construction costs at hard money rates, secured by a second position on the borrower's other properties?

The cost of not buying could be way steeper than the few dollars in cash flow you get from waiting for the perfect place.  

.- Tax Benefits: building deprecation, cost segregation, write offs etc..- Principal debt paydown: tenant paying off your loan.- Cash flow.Once the above are all added up, your true Rate Return will by far exceed your returns with stocks.Now regarding the different type of real estate, that depends on a lot of factors and mostly on your financial goals and where are you in life today.

The guys we are training in Atlanta are focusing on buying proeprties not on the MLS so they can get the discounted costs.

For your question you posed, two factors would influence my decision: 1) my opportunity costs - in other words what other options do I have at the time, and 2) My stage of life - at points in my life I have been willing to take a bit more risk, and have had bandwidth to take on that risk, and others I am not so willing to take the risk and do not have the bandwidth. 

Deduct carrying costs.

if you just pick something online and buy it - you will lose money.I like @Jake Andronico's post because he's recommending a higher cost, closer area. 

In Gary Keller’s book, Shift, he lists 25 creative options that are most common, but barely scratch the surface:- Seller Contributions- Seller-Funded Permanent Buydown- Seller-Funded Temporary Buydown- Owner Financing- Contract For Deed- Seller Second Lease Option And Lease Purchase- Seller-Assisted Down Payment- Wraparound And Assumable Mortgage- Gift Funding- Selling And Refinancing Existing Assets- Non-Occupied Co-Borrowers- Using 401(K)- Temporary IRA Transfer- Pledged Asset Mortgage- Equity Transfer And Bridge Loan- Employer-Assisted Mortgage- Lender-Funded Buydown- Fannie Mae’s “My Community Mortgage”- Running Scenarios With Automated Underwriting Systems- Adjusting Amortization Period To Lower Payment- Adjusting Interest Rates To Cover Closing Costs- State, Province, And Local Grant Or Bond Programs- Mortgage Credit Certificate- Private LendingHe said these options barely scratch the surface.