Would prefer somewhere within driving distance, which I think is doable.

Why both of them and do you prefer one over the other? 

If you can put the right systems in place and the market makes sense, I think it's an easy choice for most investors 

I’d prefer to avoid double-paying for insurance if possible.Additional Note: This property will be used as a short-term rental, which adds to the complexity.Any advice on how to structure the insurance to cover all bases without redundant costs would be greatly appreciated!

I've set this up for some of my employees who prefer gmail.

If your goal is to get the info asap for small multis, I would go with something where it's already skip traced so you can direct market or call for that investor's preference.

That said, I prefer to use a HELOC for short term investments like fix & flips because I only pay for what I use and I can continually keep recycling the money.

You can own more than one property with your VA benefits so you want to check your total allotment.House hacking with a kid is always just a choice and dependent on the proximity of the other unit and more.

This seems more of a preference item on reporting, but I wanted to get more insight on how these transactions are structured. 

I'd like to connect with someone who knows the local market as this is where I would prefer the property to be at since it is close to me.