Location (rapidly changing/close to amenities)This will hopefully make it easier to rent and give you options to rent out short term if desired.

What options are there to make this work?

Who knows.Another option would be to buy a small parcel and slowly build a house with/for him and pull owner permits.

If you're really interested in investing here I'd explore the city and network with local players.

Recently, I completed a short-term rental (STR) training program and I am eager to explore more opportunities in this field.

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Being leveraged for a bit isn't the end of the world - there are usually options available if push comes to shove - 401k loan, personal loan, sell stocks, credit card (then balance transfer continuously until you can pay the balance off) and lastly sell.

You will then have a few options with that rent money....you can put it into principal or you can start saving it to purchase yet another property.

It's a budget friendly option to some of the other services, and they have engineers on staff + audit defense, but the more expensive cost seg companies ($1500-2500) will actually do walkthroughs of your property via Facetime to more granularly estimate components of your structure. 

I did explain to them their options they had (such as sell it on the market, keep it and file BK, get a loan mod, and credit counselors out there who could potentially assist).