I'm curious to connect with any other STR/ MTR owners in that area to get more info on resources that are in the area and what challenges/ successes you have had there. 

Large apartment complexes flooded the market with inventory and are offering crazy incentives and amenities that crush the small landlord which can make finding a tenant challenging and often for less than market rent. 

The challenge is deciphering those risks.  

Over-budgeting is critical to ensure that renovations don’t eat into your profits.Market Fluctuations: If property values in your area do not appreciate as expected, or if you face a market downturn, the amount you can refinance for may be lower than anticipated.Financing Challenges: Securing financing for the initial purchase and rehab, as well as refinancing after the property is rehabbed, may be challenging, particularly if the property is located in an area with fluctuating values or if the rehab work doesn’t immediately improve the property’s appraised value.Tenant Risk: Rent collection and tenant management can be unpredictable.

The second challenge would be finding land in a decent enough area where building a rental makes sense.

Quantifying it is more challenging. 

A FHA 203k Loan is where the purchase price and rehab costs are rolled into a single loan.The downside of using FHA or a FHA 203k is you will need to live there, for a minimum of one year (to satisfy FHA Requirements); AND because you closed personally, you will not have Asset Protection, in the form of closing in the name of a LLC.

@James Zobrisky Relying on cash flow to fund future acquisitions is a challenging proposition.

I’ve seen firsthand how many STR challenges—from low occupancy to poor guest retention—can be solved through strategic interior design.

So you would spend around $25-$30k a month (this was 15 years ago) on police details and require union gate and non union gate if you had non union workforce as well.In DC area, the utility providers are a huge challenge, whether getting permanent power, or water/sewer service etc - good luck.