In couple of two weeks visits, I rehabbed it with the craigslist “proffies” for like 15K, which was not bad at the time.In retrospective, there were two things, which significantly reduced cash flow:the location- as excited first time “investor” I did not pay attention to numerous sump pumps (the house actually sinks in the swamp- not unusual in New England)the property manager- I had one great guy for the first four years (also found in craig).

In retrospect should've just added it to the price of rent and said nothing.Try it out and see the result.

I considered house hacking at one time but my wife wasn't keen on it and, in retrospect, I'm happy we didn't do it.Aside from personal preferences, it then becomes a math problem.

That one single person who has ever been accurate did so by going to the FICO website, he clicked "show me the scores used by mortgage lenders," paid $20, and I ran his credit on the exact same day & the exact same number for all three bureaus (which meant it was a waste of his $20 in retrospect).

In retrospect, I did put a lot of weight on tax rates, not so much because it was an iffy business model, more because it bugged me too much.

We have an LLC, but were told we can't get a conventional loan in the LLC's name.So, we bought a property with cash in the LLC's name (bad idea in retrospect because we can't cash out refi it and it hurt our scalability).Now, when we buy a property - it's bought with a conventional loan in one of our name's and the other parties involved transfer money into the LLC account (then into the buyer's account). 

In retrospect I have found that bank of Hawaii will lend on this up to a certain LTV which should work fine.

We've only had to turn one of them into a rental (the first one), and in retrospect, we pulled the trigger on that WAY too soon...had we left it on the market for a few more weeks, we would have gotten it under contract (most likely).Having the possibility of a cash flowing rental as your backup plan is a great idea...will definitely help you sleep better at night.That said, if I ever have a flip gone bad, I'd likely sell at a loss before turning it into a rental.

In retrospect, I should have chosen someone like that, over an out of state tenant who had never seen the property or had anyone come and see it for them either.

In retrospect, we should have considered delaying the closing to contest the appraisal.