Even the most meticulously crafted plans can frequently go off track due to unmet responsibilities or unforeseen events.This is the essential characteristic of the real estate industry.

He's essentially lost $150K.Run the numbers if he was renting it for 5 years (minus mortgage, property taxes, repairs, etc). 

This way your tenants essentially pay your mortgage while you're deployed.

Your site has got all the essential features and functionalities alright.

Interest rates are going to be forced to be reduced for several reasons, not least of which the housing market is essentially seizing up and it (with ancillary businesses) is a larger part of our GDP than many years ago when we had a significant manufacturing base, and the US needs housing to be active and healthy.

They are essentially the same thing you are describing, but sharing an "expert opinion".I am also not a fan of how BiggerPockets itself is doing this same thing in the forum by posting blog posts and you don't have the ability to comment on the posting (because some times I disagree with the posting!) 

Forming an LLC might give them liability protection and a more formal business structure, but it's not essential.3.

Understanding STR regulations in a market is an essential "must do" when it comes to evaluating a short term rental.

Also, what others have said, the personal touches on what is in your place (e.g. providing all the essentials instead of having people buy TP, coffee, shampoo, etc.) and the quality of those items (no tattered towels, stained sheets, etc.).  

Part of my issue was not having a reasonably priced handyman ahead of time and eventually overpaying to just get it done and also inexperience as a manager.With that said, you essentially have two options: very cheap properties in less good areas (you're looking at 100k or less--which you might have trouble getting a good lender for)  or trying to do some sort of house hack (e.g. live in flip, live in rent by the room, multifamily) where you budget will be closer to 200k-300k.Personally, I would not look at real estate until you are maxing out your 401k and IRA, but lots of folks have done significantly better with real estate than stocks and would think I'm crazy for suggesting this.