I never sit down like Scrooge and count my money.I have absolutely no financial goals, but I figure that if I am going to work an 8, 10, or 14 hour days I am not going to do my very best during those hours.

Appraisal= $258k/ purchase price = $230k/ Built-in Equity= $28,000/ Down payment cash $27,000.I have $27,000 cash to put into a down payment on the above home BUT, I need to use some (about $10,000) for a new roof/gut...

Or can I just count the cashflow as income?

Banks are not counting this income yet.  

I’m not sure how long it’s lifetime is and whether or not it can be counted on to cash flow.

The VA will be lifting the V loan limits so if you find a fourplex they may be able to count that income as part of your loan.2.

I have been reading that up to 4 mortgages are easy to get and instead of the total amount on the mortgage the count matters.How would these two compare?

Hopefully your income is relatively high because some lenders will count your HELOC as debt, even if you haven't drawn on it. 20-25% down will get you better terms and more flexibility, plus it forces you to stack cash.

I have been reading that up to 4 mortgages are easy to get and instead of the total amount on the mortgage the count matters.How would these two compare?

If so, then you're not making $140k.What counts as your income is NET income, or rent minus all expenses: mortgage interest, property taxes, insurance, maintenance, repairs, depreciation and more.