In retrospect I should have done more research before I made the trip.

In retrospect, that 5K was a drop in the bucket compared to cashflow it eventually produced but while it was happening in the moment...

Everything I’ve flipped I wish I kept in retrospect, as flips are often just a good tenant away from being a brrrr. 

In retrospect, 10% cut for zero headaches sounds like I steal, but I just don't know if such a property manager exists around here for a landlord with only one rental.As to your other ideas about a 90 day lease before a year or longer lease.... there was definitely zero smoke or pets in his first 90 days, so that wouldn't have helped in my situation. 

I passed on a lot of deals early on that I thought at the time were just okay but in retrospect would have turned out excellent.

As such, my belief is that the market price in any given local market within the US is probably the fair representation of its valuation, considering both future appreciation and current cash flow.A retrospective mathematical modeling of the past performance of various major US markets might be interesting.

I sold my first one and wish I hadn't in retrospect. 

We're sorry you're unhappy in our property and after some consideration have decided to allow you out of the lease with no penalty so you can find more suitable housing.We did this once and it was an excellent idea in retrospect.

That just reminds me of waiting to buy into the stock market because you think its going to go lower, or you wait to buy in because you think its overbought, but it just keeps going up and you look in retrospect thinking "I should've got in sooner."

Which in retrospect I would have done the HELOC while I was still owner occupant of the property because I would have gotten a higher LTV.