He is going to have a very difficult time refinancing unless he has a extremely large downpayment.

I spent 100% of my liquidity to buy that first house in Milpitas CA and that set me up for the rest of my career basically..

Several things are red flags: the low purchase price, especially for a duplex, almost certainly means one or more of several things: it is in an undesirable neighborhood and it will be difficult to manage, they didn't do much on the rehab and it will have some very significant differed maintenance, it will be very difficult to exit without a loss because it won't appreciate. 

I'm also having difficultly with monthly reports.. when i export to CSV (w/ Airbnb) for monthly reports it exports to an Excel spreadsheet that is not the most convenient to use.   

Homes with only one bathroom are difficult to sell no matter how nice they are.

The people who get in trouble are the ones who bend on their criteria to make a "deal" work because it's difficult to find something that actually fits their original criteria. 

As difficult as it may be, you have to stay rational about this and don't let your emotions make you say things that you'll later regret.

Capital growth here is really muted and the virus like de- gentrification in some areas can be difficult to pick.

I wanted to see if I could get some advice/guidance on change that I am thinking about making in my career. 

I look forward to reading more about your investment career and hopefully Ill be able to follow suit with my first one.