I wish I had bought two that day.

Best wishes! 

I’m a lender working with real estate investors on fix & flip projects, and I’m curious—what’s something lenders consistently get wrong or overlook when working with you?
Looking to learn from your experiences so...

I wish I had added Airbnb a month after I felt comfortable with my PMS and Vrbo.I wish I had worked harder to achieve an earlier date-placed-in-service for tax purposes.I wish I had attended the Avalara MyLodgeTax Lodging Tax 101 within days of closing to understand all the state, county, and local taxes and licenses.I wish I had known I was responsible for collecting and remitting taxes from Vrbo bookings because of the API connection to my PMS.I wish I had hired one cleaner at a time from Turno to build trust with one another and pride in keeping an orderly supply closet.I just hit the first anniversary of the date-placed-in-service, and there might be other “wishes,” but these are what immediately came to mind.I would bought as many properties in 2008 as possible! 

Quote from @Mike Grudzien: I wish I had a better answer, but there is a current trend to the bottom with STRs (some markets are exceptions). 

Do you wish you would have had an LLC prior to your first investment purchase? 

Things I'd wish I'd known earlier: don't sell off a California property because it's getting a little rough (it was rented out then market declined).

It is scary to start out, we've all been there and wished for someone to watch over our shoulder when we started. 

👎What do you wish had gone better? 

If you’re seasoned, I’d love to hear what you wish you knew when you were starting — or how I can bring value to you.