Recommendations On Next Real Estate Move For Beginners

[Carlos Lopes]

Current situation. 

Own a rental single family home in SW FL that cash flows about $1000/month (after all expenses, and my insurance nearly doubling over the last year). I am currently in the process of purchasing my next primary home in GA using a VA loan and my own savings as a down payment.

Once I purchase my new home in GA, I’m wanting to keep buying more rentals and start building a portfolio, just not too sure yet on what approach to take.

Currently, my rental home in FL has a decent monthly cash flow in my opinion. Used to be about $1,300/month, but after the hurricane, insurance has doubled and property taxes have taken a dent on that. Regardless, It’s always paid for itself and allows me to build a savings for its own repairs when it needs it, so overall I think I still have a good rental situation. Lastly, I have about $160k of equity on that home. 

I am fortunate to have a very good paying job, so saving for more investments is not an issue, and the risks I’m willing to take can be a bit higher than the average beginner in real estate. I’m definitely not looking to house hack, and not sure how I feel about flipping yet since I’m not that experienced. The thought of short term rentals attracts me.

Given current markets and my current rental cash flow on my one rental, what are some thoughts on selling the rental and using that as a downpayment for a nicer short term rental elsewhere? Or would I be better off keeping it since it’s cash flowing (been this way since day one of renting it 4 years ago), saving some more of my own cash again, and just investing that instead into a short term rental property? Or should I scrap short term rentals all together and maybe look into MFH instead?

Just looking for overall strategies and what people here have done that’s worked out pretty well. Thanks in advance guys.