In the future, we aim to get into fixer-uppers, development, etc., but for now, we like to only consider semi-stabilized (with minimal deferred maintenance) or fully stabilized, cash-flowing properties. 

This is going to do two things to help you in the future to free up your VA entitlement so you can buy another home 100%. 

Determined to avoid such mistakes in the future, I earned my real estate license to better understand the buying and selling process.

Will report back on the hobby vs business endeavor.

It really comes down to running the numbers and seeing which option offers the best balance of costs, monthly payment, and future flexibility.In short, a DSCR loan might work, but it may not be the cheapest or most suitable option if a second-position loan or HELOC can accomplish the same equity pull with fewer costs or better long-term benefits.

If you decide to join, take their claims with a pinch of salt and conduct your own due diligence.My experience has not been positive so far, but I am hoping for improvements in the future.

Always vet each property thoroughly as the past does not equal the future. 

This will go a long way in creating a network and future sellers and buyers will start to see you as a resource in this arena.  

I would love to make a move before the end of the year and so I keep trying to decide which of the following is best for me:1) Buy 1 more expensive CA property near here, and thus a better tenant (less likely to cause issues), but lose a little bit of money every month due to the current numbers, while hoping for future appreciation? 

You will have to gather more accurate operating costs (vacancy loss, taxes, utilities, insurance, mgmt fees, maintenance, HOA) to best determine potential future performance.