As the owner of a property management company in Washington, I have encountered this situation before.

Now we are in 2025 and although I still own the trucking company, it has been an inconsistent pit that has technically brought me personally no profit.

@Andrew Self I would like to think that my company is the best and offers the lowest rates and closing costs, but perhaps I am bias.

@Obed Calixte The memories that bring me joy from a career perspective are the times when I've had the good fortune of delivering an above-projection return after a successful investment round trip. 

Depending on the repair (reroof, new electrical system etc) reputable and solvent contractors can be open to being paid at closing.There are also third party companies such as Curbio that can be a fit for this situation.

I have had PMs successfully get large reimbursement including this PM got one last year (but I do not remember which OTA).It is my belief that AirBnb rejects some smaller claims hoping that it is not worth pursuing.  

Depending on your down payment (which it seems like you have a good amount of liquid for that) they can nicely cash flow.Ultimately, success in real estate investing comes down to choosing a growing market, investing in a good neighborhood, and building a strong team to support you.

Brett,I have never heard of that company but any reason why your not using an FDIC Bank or well known lender? 

G'Day Alejandro,As a few have already mentioned, take a peak at Toledo also.In my opinion lower potential for long term appreciation but solid/"boring" cashflow.I prefer my portfolio to be "boring" but cashflowing lolLow entry points (Sub $100,000), high rents (Above the 1% rule).Blue collar working class decent folks that will stay and pay.Depending on the area but no derelict homes, yards well kept, cars with wheels and all tenants are employed.Plus, all are sophisticated enough to pay rent online so property management doesn't have to collect rents with bullet proof vests and shot guns lolI'm bias toward Toledo but it's worth considering.Wishing you much success

The successful wholesalers are the ones that are direct with the seller and have done an analysis on the deal to show it can be a successful investment (always double check with your own)totally agree, I would add the don't act sketchy and present their available homes in a consistent/professional manner to buyers.