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

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? 

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.

Jacob,Good points, and I support your ideas about giving back.

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.

now, if you want to buy an STR as an investment, and you NEED the income to support it, that's totally different...

If you see at least a few zoned in the designations you mentioned above, that's potentially a good sign that you can get support from the local Alderman's office, and approval by the ZBA (zoning board of appeals), to rezone.

Given all your data on historic pricing, average length of stay, and pricing at the 25th percentile, please let us know if you're able to push up the VRBO chain to speak to a Supervisor (or equivalent) and have them verify the data that supports your position.I can share that calling the VRBO support line: 877-202-4291, identifying yourself & property ID, and requesting a Supervisor politely and repeatedly, can lead to different outcomes.

It really comes down to investing in a growing market, in a good neighborhood & building a great team to support you.