I really like / prefer the 14 unit property due to its lower asking price but CAN NOT afford to hemorrhage money monthly like it currently is.

There are 4-plexes in the south end that are well within that price range,  but you will be dealing with a lower socio-economic bracket of tenants that you are probably used to with your townhouse.  

Like you, the higher market has given me an opportunity to prune lower performers and re-invest in better deals, when  I can find them.  

The interest expense on the loan would lower the taxable income on your investment.

I would like to know... when you analyze a potential rental property deal, do you "stress test"?

Do I continue with the deal knowing that the cash flow is lower than expected but just get into action or wait until another deal and continue waiting knowing it's a sellers market? 

However their taxes assed value are all above $50,000.So my question is, can someone provide a step by said process on how to argue a lower tax amount .

I'd rather not ask my agent to continuously make offers with a 1 in 20 success ratio (or lower). 

Those are usually lower-risk people.You also said he has "significant savings" so maybe he can pay a triple deposit (if your state allows) or the first few months in advance.

The second recommendation would be to do a house flip with a special and your able to move there and be a "house hacker" and take advantage of the lower down payment.The only other way away from home is to buy an apartment complex that had a minimum of 30 units so that project could afford property management company from that local area, they need to be experienced and understand what you expect in reporting and current operation with phone talking.