Overcoming fear - first investment!

[Tyler Relph]

Looking for some guidance (and a vote of confidence)...I currently have a VA loan on a 3/2 that appraises for 165K with a loan of 149K (mortgage just under 1100 including P&I, taxes, and insurance). Current rental rates per Rentometer and Zillow show comps of 1300-1400/month. I contacted a VA mortgage company and got a pre-approval for a second tier entitlement, which allows me to utilize the remainder of my 417K entitlement with no money down. I will have to do some work to my current house to make it rentable; however, I estimate these costs to be around 5K. My fear lies in taking on two mortgages. Granted, I hope to rent out the my 3/2; however, in the event that it sits vacant, how do I overcome the fear of taking on two mortgages? Is this sink or swim feeling normal for newbie investors? BTW the new property is a double lot that has a home priced at a single lot rate. Initially, the property was listed in May16' at 329K and its now down to 280K. Looking to offer 250K and negotiate to no more than 264K. Once the other lot is sold, it should pocket us 90K. To me, this makes great sense; but, I'm still nervous about taking that first step.