But to answer your initial question, there are lenders that will lend on longer terms.

Is real estate truly worth the stress and initial investment (down payment, closing costs, repairs/updating)?  

If so, the expenses will be deducted on Schedule E along with your rentals.Wholesaling, like flipping, is a business activity only once you have an initial property under contract.

.- During that initial week of escrow that the buyers are rushing around getting things done, mom dies, and the buyers frankly do not have the emotional strength to go through with this at this moment.

Buying the right house for your retirement, every time you PCS.Just some initial thoughts.

How do I make sure that the bank will approve my initial offer?

Google "FHA seasoning guideline" or something to that effect for more info, but essentially it has nothing to do with what your initial question was asking.Btw, I sent you a message back earlier today to email me.

If the value is there you can actually pull out your initial investment, purchase price plus closing costs with delayed financing right away. 

And do you feel as though the 2008 downturn, ultimately killed your initial dream?

It will cost more to establish such a structure initially, but can save you a lot on paperwork, delays, and processing fees over a few years of investing.