Now I am starting back calling many banks to find the best conditions.Please note that you should look at either mid size or small size banks...

I would price out the plumbing and electric for the smaller stacked units (think ge space maker or smaller) in the units before a free standing building....you just need a closet size space and they do this in the efficiency units (450square feet) where I have a condo rental..this may put the costs for electric back on tenant if individually metered..

Like you as a mortgage underwriter, I have many years of experience being a professional supporting real estate investors as a CPA, but I now wanted to become a real estate investor myself.In late November of last year, like you're doing this November, I wrestled with the question of investing locally with a 4-unit purchased with FHA financing vs. investing out-of-state and got a lot of great advice.Like you, my goal is to retire within the next 10-15 years via real estate investing.As a result of some of the advice I've read through the forums (I would recommend you pay attention to guys who have been in real estate for decades like @Jay Hinrichs rather than the younger folks who are often just pushing their turnkey products) and speaking to investors at local real estate groups, I decided that given my place in life I would be wiser to place my bets on California appreciation over the next 20-30 years rather than investing in some beat-down property in Cleveland for an extra $400 or whatever in cash flow per month.Given the facts that (1) I could get into a property for a measly 3.5% down, which would free up cash to invest in other places if I so chose, (2) I was already throwing away rent every month such that I could still be cash flow negative of $650/month (what I was paying in rent) and still be better off because a portion of my monthly payment would be building my equity and the rest would be tax deductible, and (3) I'm in my 20s and have the time to take a long-term view of appreciation potential, it was a no-brainer to go the FHA 4-plex route in LA, despite the fact that it is one of the most expensive markets in the country.This isn't to say that the process was easy.  

Then you can back into the size of property and location.

Let's say the tenants are only covering a portion of the mortgage/expenses, and I have to pay $1000 out of pocket.

Now before i get into what YOW is, It is important that you know how a corporation of this size works.

These payments could be made directly if we had the cash or ask the bank to pay a portion of our sanctioned loan.

You can also buy a physical mortgage calculator, or use a financial calculator.In addition to monthly PITI you will need to know (or estimate) what portion is tax & insurance, to get to just P&I.Then you'll need to know (or assume) a term (length of loan) and interest rate - that will get you from P&I to loan amount.  

2. is it possible to find out tenant's portion of the rent prior to the lease signing date?

It's really hard to get an idea of cost without someone actually going out to bid the job (not knowing the size, location, grading for the lot, whether you need to add curb cuts to enter this new garage from the street or if it's from the alley, routing utilities, etc).