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? 

If you want to acquire more real estate I suggest more savings or sell the other property with equity. 

We plan to stay in this house for more than 5 years unless another great opportunity arises, but maybe it is best to allocate a bigger portion of savings to our real estate investment savings account than our home improvement savings account for the first few years.

@Drake BackmanBigger Pockets is a great place to find a tax strategist specializing in real estate taxation.A good real estate tax strategist can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding a tax  strategist specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year.

I'm looking for you advice with my overall strategy and garner any experience you might have to save me from learning the hard way. 

There are hundreds of hard money lenders out there, ultimately I'd work with someone who has time to focus on ensuring you get a tailored mortgage instead of a cookie cutter solution.

Start with BiggerPockets Ultimate Beginners Guide (free).

Ultimately, it’s about aligning your goals with the right strategy.Makes sense.

I also ask if they've ever been evicted, refused to pay rent, or filed for bankruptcy.Further, I ask account numbers for their checking and savings accounts, and the approximate balances in each.

Best to hire it out, even though it hurts the margins, it saves my time and stress substantially.