I've found that having a good team of people who trust each other, stay in their lanes, and communicate are the biggest reasons we have succeeded.

Parking will likely be your biggest hurdle.

I've flipped about a dozen properties here in Chicago, and quite honestly, it felt like something different went wrong on each one of them.My biggest piece of advice is to KEEP IT SIMPLE starting out. 

The biggest red flag is discouraging you from viewing the property in person.

The biggest risk I see is one decent size hiccup and they could be toast.

- Network with local agents and investors, so you start getting first crack at new deals.If you can amp up the cashflow on the first duplex, you can use the extra cash to:- Pay down the mortgage, setting yourself up for a future refinance to free up your VA Entitlement.OR- For your next acquisition.One of your biggest challenges will to keep the cash flowing when you move out of a duplex.

Dishes are the biggest conflict in almost all roommate situations.

In my opinion the large population (too many people) is the biggest issue in San Diego.

I think one of the biggest risks you face with Cash Out is interest rate risk.It's really difficult to predict where interest rates will be in a 2-5 year time period, so it can also be challenging to model out future mortgage rates.

To me the biggest issue with out of state investing and long term rentals is that you have to deal with property damages and/or evictions.