•Breaking even in Year 1 is reasonable, and cash flow is possible with good management and pricing strategies.

When you specifically mentioned STR experience and the possibility of something with some added "personal value" bells started going off. 

Each property qualifies on its own economic merits (i.e. rental income covering PITI payments)This is one of the main advantages for DSCR financing, i.e. the ability to scale without any kind of DTI limit imposed by conventional financing.

No financing available.2.

Financing your second property can be tricky since lenders may only count 75% of rental income toward your debt-to-income ratio, so get pre-approved early.

Now that I have answered your question, I'd like to share my questions and possible concerns. 

Hi Jayce, we got the seller to carry back the portion of the down payment and the bank to finance the 1st position on the rest.

You can finance it with an FHA loan (3.5% down) or a conventional loan (5% down) if you plan to live in the property.

Now days you don't buy a deal you make the deal either with how you operate the property, how you finance the property, or how you purchase the property.

Assumed nothing could possibly go wrong in the next 5 years what you want when you look at an investment property is to know the current rental amounts, specific expense items, and conditions of the building, grounds, and mechanical systems.