The fact that you've kept the same tenants for 4 years speaks to the stability of the rental income, which is key for buy-and-hold investments.Your strategy of house hacking and then moving into a rental property was a smart way to transition, and it’s clear that the live-in flip helped you build value.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

We are open to investors helping us, but need to learn more about this process as well.  

I'm here to help with any financing needs or further advice you might require!

I own a PM company in Birmingham and we help a lot of OOS investors with their Section 8 properties. 

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

I enjoy helping and talking REI to help other members avoid mistakes.

They should be able to help you out with this.

Hope this helps!

Some questions to consider to help determine the best lender for your situation:What's the loan term length & down payment needed?