It's not perfect because I still don't know Memphis market well but I count on my PM / provider to help me.Can I do the same using a local realtor?  

The bank I use primarily in Colorado will count 75% of my projected rental income towards the debt when I buy a new property, so in the case you're providing above, you're creating a nearly $1000 liability for yourself from a DTI standpoint every time you buy a property.

The mortgage payment would NOT be counted in your monthly liabilities, because it's already accounted for in that $300 calculation.Yes, if you include additional expenses like a management fee, or commissions, maintenance, advertising, etc., those would not be added back and they would reduce the amount you can qualify for.You take Schedule E profit of $3,734, and add back interest, insurance, taxes, and depreciation. 

So even if say I thought maybe I'll try to milk a few more years out of old furnaces, NO WAY do I count on this. 

You can't count the tips as they are not guaranteed.Even without all the other flags, you could reject just on income.I would love to hear how he would spin the answer to the question "are you really trying to tell me that a skycap making $2.13 per hour was asked to relocate?

I got the feeling she was hinting it will never be an issue and I don't need board approval.That said, if the appreciation keeps up, I could gain around 45K in the first year after I close on this house, and so forth, not counting principal pay down, cash flow and tax benefits.

From my understanding, lenders will not count this money as income towards a loan.

Or am I double counting? 

Most people don't count principle when analyzing a deal.  

They can also keep the land and do a ground lease.I usually look at traffic counts for the area and what they are doing year over year.