My thoughts: if you have a steady job that can support the negative cash flow, and you don't plan on leaving Long Island for at least 5-7 years, I would house hack. 

He didn't apply, but you know she's a good mom and would only date a guy that's good for her kid and supportive of her goals, so you ignore the little nagging voice in the back of your head.

Is it a small town with one factory supporting the town?

Depending on your down payment (which it seems like you have a good amount of liquid for that) they can nicely cash flow.Ultimately, success in real estate investing comes down to choosing a growing market, investing in a good neighborhood, and building a strong team to support you.

THEN, I plan to purchase the second home using a FHA or conventional loan (3%-5% down), for which I will likely pay the monthly cost out-of-pocket, maybe with some rental income support if it is a duplex.My concern is, I do not want to spend my savings or weigh down my debt-to-income ratio so much so that I cannot qualify for and pay the down payment and closing for the lending on the second home.Questions: - With the first home being multi-family, 75% of the rental income (or potential rental income initially) will relatively either maintain or boost my debt-to-income ratio from lenders' perspectives, right? 

Some of the best investments can be found in neighborhoods where you may not want to live, but the numbers support it! 

While I’m not an investor myself, I work with highly trained VAs who support real estate professionals in generating direct-to-seller leads.

You have to know the market before you build a plan and I don't think this market supports your intended plan.

That said, if you have a very specific issue, please contact support@biggerpockets and perhaps they can assist you.

Here’s a bit more information about why these could be such powerful tools for you:Financial Support: The average benefit for buyers who qualify for down payment assistance is $17,000.