Significant and sustained population growth with a metro population >1M.

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.

Year 0: ($2,000 - $1,700) x (1 + 2%)^0 / (1 + 5%)^0 ≈ $300 in today’s buying power.Year 5: ($2,000 - $1,700) x (1 + 2%)^5 / (1 + 5%)^5 ≈ $260 in today’s buying power.Year 10: ($2,000 - $1,700) x (1 + 2%)^10 / (1 + 5%)^10 ≈ $225 in today’s buying power.Year 15: ($2,000 - $1,700) x (1 + 2%)^15 / (1 + 5%)^15 ≈ $194 in today’s buying power.So, if you purchase property in a city where rent increases at a slower pace than inflation, the amount of goods and services you can buy will decrease over time due to inflation.Here is what I recommend:Purchase in a city that possesses the following characteristics.Significant and sustained population growth.Rapid and sustained appreciationBalance negative cash flow, interest rate buydown, and increased down payment to create an acceptable cash flow situation today.Refinance when rates fall to increase cash flow.

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

I used a HELOC to cover the down payment, appraisal gap, and furniture, allowing me to enter the STR market without depleting cash reserves.

For this reason, it would be prudent to not overleverage yourself in this type of environment in order to wait and see where rates do end up falling, as there is consensus in the market we are moving into a falling rate environment, the exact timing of when rates will be falling is unknown and different scenario analysis should be added to underwriting refinance periods to be sure the project is sustainable if inflation resurges and a refinance is delayed.

The ones I see all need some dollars to get them ready over and above the furniture.

Who knows one day I might give it a whirl it’s just I did not want to buy a whole bunch of furniture on a maybe.

While cashflow isn't my primary goal while I am growing I still want enough that the business sustains itself without requiring my W2 income to keep it afloat. 

It's not sustainable.