Will the title company put this property under our LLC name, and won’t be required to legally inform HUD/tax authorities. - will it influence property taxes once we move to conventional loan in 3 yrs? 

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.

How do you pay for the tax and insurance?

When you add that: "The downpayment and closing costs would be one large hurdle"; I can't tell if you can only afford to do this once (thus tying up whatever you have saved) or multiple times.  

I always like to look at several years worth of property taxes.

The patent on the 30 year with taxes and insurance was 3900 or so.   

Finally, short-term rentals can offer potential tax advantages, as many expenses associated with the property may be deductible.

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

Post Dodd Frank sellers have continued the same bad practice of selling houses to occupants with financing at selling prices that are way high, can't be justified via any type of 3rd party valuation (appraisal, zestimate, tax value, even recent sales in the same area).   

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?