Buying cashflow-negative properties? (massachusetts)

[Alex Silang]

Hi everyone, this is my first post. I live in Boston and am an aspiring buy-and-hold-investor. The prices here are ridiculous. I'd prefer to rent to college kids. Usually they are getting the money from their parents, they tend to be from well off families and the market is plentiful.

Here is an example from a realtor.com listing (tenant is really paying this rent amount):

$195,000 asking price

Rent $1150
Management fee (%10)
Revenue net of fee - $1,035

$790/mo mortgage
$210/mo property tax
$ ? / mo insurance
$250 condo fee

We are already in cash flow negative territory and that is without factoring in insurance or repairs.

I am a long-term, buy-and-hold investor. I'm okay with buying a property losing money in the short run if it's worth it. But is there anyway this could work? When looking at cashflow-negative properties, what should one look for?