I will probably want to refinance at least 80% of that into something fixed at some point to hedge against rates going up.Monthly costs:* debt service = $441 (141,000 *0.0375/12)* insurance = 78 (quote from Geico)* HOA: 860* taxes: $149 (it's $894 each per year)* repairs: $100 (I'm estimating a little less than with an SFR because with a condo I don't worry about the roof, the hot water heater, landscaping, etc.)total: 1628Monthly income: $2660 (1410+1250)Net: 1032Cap rate = 8.7% (1032*12/141000)Things I didn't include: closing costs, vacancy.

@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?

Also there are plenty of other financing options than the standard 20% down deals.  

FORECLOSURE: A seven year waiting period is required, and is measured from the completion date of the foreclosure.A three year waiting period is permitted if extenuating circumstances [EC: non recurring events that are beyond control that result in a sudden, significant and prolonged reduction in income or a catastrophic increase in financial obligations]  can be documented and the lesser LTV of 90% or the standard product guidelines.

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