Many others have given some great advice here and I do agree, $25k could maybe get you into a small condo somewhere but there are still closing costs for the loan, furnishing, and it would be wise to have more set aside for unexpected expenses when setting it up as STR. 

We just had our 2nd property go through eviction within the first year of owning, and another had an unexpected turnover at about month 15 (they had 'just' signed a new lease).

If you do not understand these documents, you can easily end up getting an unexpected Special Assessment or big increase in the monthly fee within the next 2 or 3 years.

If you have the capital ready to go to cover: down payment, closing cost, any necessary repairs once you buy the property, plus cash in reserves for unexpected costs, there’s no reason to wait for prices to come down (they may never). 

I needed to get the addition done right away for my mother to move in due to an unexpected death, so I planned on getting the permit done within the year or so.

When you apply all revenue from the rents to paying the debt service, you will be relying on reserve funds having to come from some other account should some event occur that would normally draw from reserve (some examples are replacing roof, replacing heater, handling an eviction - there are other such events).Be certain you do have reserves to cover your (somewhat) unexpected expenses.

If I do very basic math, I can see I am making profit but to look at the cash flow, I am adding other expenses such as - Property tax, monthly association fees, property unexpected expenses, vacancy...

Implement expense approval processes to manage and control spending.6) Cash Flow Cushion: Build and maintain a cash flow cushion by setting aside a portion of cash reserves for unexpected expenses or economic downturns.

Did you encounter any unexpected challenges or opportunities during this transition?

Like @Evan Kraljic said, having capital for the flip is very important and only having $15k may not be enough of a buffer if something unexpected comes up (especially as a first time flip).