The mindset for many lenders is, "if you have to pack a lunch for a site visit, it's outside your area of expertise," which at this point the deal is effectively a gamble.

I have two questions.(1) How does that effect the underwriting and ultimate mortgage I may obtain?

Having a MA construction license allows me to be cost effective for up-fits or remodels so a flip here and there is always something I am looking for as well. 

Looking for most cost effective solution!

Effectively paying $23,723.64 more at the end of the 30 yearsThat means on average, each month by saving $8,000 upfront you will be "Losing" $65.90 a month for 360 months.

Get a mentor to help you and always Check with an attorney to assure you are in total compliance.I build new for rental primarily for the following reason: 1) I am a builder and have the KSAO's (knowledge, Skills, Abilities, and Other) means necessary to efficiently and effectively build; 2) I buy all my land substantially below market value (usually off-market); 3) any land I buy at market has an immediate value-add component that can quickly make it worth more that what I paid for it; and 4) Cap Ex is generally MUCH less for new construction which means a stronger cash flow up front, but you are always going to need to maintain a suitable Cap Ex account if you are truly going to hold for more than I'd say 7-10 years.... but everybody has their separate opinions and thought process concerning what the "right" amount to designate to Cap Ex is proper..... 

I just got bit in the rear b/c Albany reassessed my property for what I paid for it (duh), which effectively doubled my property tax liability.I'm owner occupied, and with my first purchase I was primarily concerned with simply making sure the income covered operating expenses, and not terribly concerned w/ driving profit, but I was relying on the ~$200/mo I was making above cost to help subsidize fixing up the building, and now I'm about $50 south of the property costs.Paying $50 a month to live in my 4-unit isn't bad, but if this was a classic investment property, I'd be pretty ripped :)

I noted the fact that many people focus on three income streams that are least effective for building wealth.

My neighbour sold his house a week before the new mortgage rules went into effect for 200K over asking and literally a hundred people went through it, and last week my friend put his house on the market (nice house, great area) and only one party made an off at asking price...telling perhaps, but would be interested to hear what realtors are noticing.

If you still want to manage the property yourself, the first 3 are all good, but may not be cost effective depending on how many units you're looking to purchase.