@Michael Plante We live entirely off a base salary after taxes of $4562 a month ($1000 mortgage, prop taxes, insurance, food, vacation savings, etc) and I also make about $5000 a month in commissions.

I would prefer to stay away from FHA loans/fees if possible, but am open to scenarios where I can still make the numbers work with all fees/insurance.

You don't have to run this through title insurance, because you are deeding this from yourself to an entity that you will own or control.  

Make a spreadsheet and take your total rent and subtract vacancy, mortgage, capital expenditures/Maintenance, Tax, insurance, and property management (You always want to include this just incase down the road you end up using property management).

With this same property and an estimated rent at $1000 a month here are the numbers:Mortgage $485 (75k at 4.75 for 20 year amortization)Taxes $100 (This is a guess because I have no idea what they would be in your properties area)Insurance $50 (This is also a guess but I am basing it off of my own rentals)Property management at 10% $100 (This depends on if you will be managing it yourself or not)Capital expenses savings for repairs 10% $100Vacancy 10% $100Monthly cash flow = $65 (6% APR rate of return on your 13k left in the property).Now there are several variables in this example.  

Do I need to check with the insurance company?

@Brian LeskoWithout looking at property, these are just a few that come to mind, of course some of these are a bit to soon to ask during a showing and even the realtor may not be prepared or know the answers to these, but eventually if you want to proceed with this property you should definitely get answers to these:How long have current Tenants been there?

Then proceed as a lease option

How much is the typical home insurance with standard liabilities cost for multi-family units around Boston areas? 

But went about it this way because I am closing on other properties in my own name right now so we used just the father's financials to qualify for this particular one, and the mortgage market does not allow lending directly to an LLC anymore.Simply put, our goal for tax reporting is to divide all rental income for this one property equally in to thirds, and to do the same for all expenses (mortgage interest, taxes, insurance, repairs, etc.).