I'm actively working through this process somewhat now so I can roll funds into a bigger boutique hotel project.

I tend to do a quick dirty look at a building like JW with price per door, but after that sniff test, I quickly like to understand $Cost/SF and $rent/SF.The way I look at a single family, 2-4 units, or a 20 unit is all different, but the end result is still ROI or IRR (over time). 

It's really not that difficult, only takes an email or two to the local creditor's rights attorney in the state to get the ball rolling. 

It was a test, sounds like not a successful one.

Ensure the rents and expenses support the debt service and provide solid cash flow after covering the assumable loan, seller carry payments, and operating costs.Occupancy & Rent Roll: What’s the current occupancy rate?

I generally agree that buying SFH as first investment is an easy way to test the waters; however, if you’re set on REI I suggest buying a duplex or quad.

As mentioned elsewhere, breakeven on cash flow is not the same as break even for taxes.Let's make some assumptions:Rental income = $1000Mortgage payment = $400 - but $300 is interest and $100 is principalOther expenses (repairs, advertising, utilities, etc) = $600Depreciation = $250The above scenario creates a break even from a cash flow perspective, however the tax scenario looks like this:Rental income minus the mortgage interest (principal is not deductible) minus the other expenses minus depreciation looks like this:1000-300-600-250 = $150 LossIf your income is over $150,000, then you cannot deduct that loss, but you can roll it over to future years. 

They can test even the sharpest investors.Another buddy of mine, who’s based in Austin, had a client that found herself caught off-guard by a last-minute inspection delay on her Oregon property.. from what I’ve heard in Forbes, the local market’s short supply of exchange-worthy replacements didn’t help either.

My 2 cents is right there with the other guy, get into something on your own first to test the waters and know what it’s like to actually buy and do some work.

The no is a test to see how they will take it and respond, whether they will listen.