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.  

That can make the difference between a 40k per door property and a 125,000 a door property.With the online retail business a lender will want to look at how stable the cash flow has been year over year.

You'd be doing well if you could find something even slightly undervalued (which is likely your realistic best case scenario as an outsider coming into a hot sellers market), meaning that it will probably need a little work or updating.Lastly, whether you're able to find something technically below market value at all or not - I'd buy in a stable, desirable area/neighborhood.

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?

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