I love the flexibility they offer for traveling professionals, military families, or folks in between moves.My main questions:Have you noticed increased demand for midterm rentals in this area, particularly from military personnel at nearby bases or healthcare workers at local hospitals?

@Scott VaethIf you live in part of the home and rent out rooms, you might be able to keep the lower 4% owner-occupied rate.Instead of a long-term rental that barely covers half the mortgage, could you do a rent-by-the-room model or target traveling professionals to increase cash flow?

He spends $4,000 in travel expenses looking or new properties to buy.

I have 0 experience managing STR properties, but lots of experience using Airbnb from my travels 😅 I am halfway reading Avery Carl’s book on STR.

Meaning you can spend the time traveling to the market(As we did for 18 Months once per quarter) or you can seek a reputable operator in the market you want to invest in and leverage their team. 

I offered them asking price on all of them as a package with 50k down, amortization for 30 years and balloon out in 24 months.

Let's assume the financials in the package are good for a moment (they probably are not) AND that you either do not or do achieve the broker's pro forma:If you purchase this asset, achieve ONLY the 'current' NOI, grow NOI 2% per year, and exit at a 5% cap at the end of Year 6, you will have a 4.8% unlevered IRR. 

Now as a frequent traveler often to mountains, I always book hot tubs. 

Appreciation is unlikely, and selling later may be tough.Challenges of an Out-of-Area RentalLess control over tenants & maintenance.Emergency costs (travel, major repairs).Harder to sell if the area declines further.Better Approach?

Absolutely - East Hill is a really popular area for traveling heath care professionals, as well as military on short term TDY orders who are looking for furnished stays.Keys to success for my condo have been keeping the furniture fresh, and not looking like every other listing out there.