But in retrospect if I had managed it better or made it repeatable it could have been better. 

In retrospect, I should have made everyone fill out a paper application.

In retrospect, we should have torn it down and built it back.

You are putting yourself (your capital) at RISK in a potential sinkhole.I am somewhat experienced, and rehabbed a 1960 building (and it came out OK) but in retrospect I could have razed the house and built new and made even more money.  

I would still consider this a bad deal on paper, but.....In retrospect, that was the most important property I bought because it got me a seat at the table.

We ended up closing the round in time, but in retrospect, accurate planning would have been tremendously helpful. - Chenyu Ren, Markai, Inc.2.

Retrospectively, wish we had just stayed with OOS investing, and bought in Big Bear, but if you are going in looking for a STR from the start, you might do okay with something close to downtown.

A licensed appraiser can do a retrospective appraisal and tell you what your home would have been worth at the time you converted it to a rental.Now, addressing the depreciation basis is relatively easy.  

Orita, I was faced with the a very similar question a few years ago, the answer is more complex and depends on your goals, so I decided to write a blog post about it to shed some light on the criteria I used in FInding a good home for my capital  - https://www.biggerpockets.com/blogs/10305/67660-fi...As for leverage, I too purchased properties all cash in the beginning, but in retrospect, I would use some leverage, not crazy amounts but something you are comfortable with, for me that would be around 60-70% ARV.

He explained that once when he was audited, he had to pay a higher amount on workers comp (workers comp is retrospective, initial premium is projected so the total premium is paid at end of coverage period).