I have confidence you have not as your maintenance/cap ex estimate would be significantly higher if you have actually calculated a value.

As far as investing in the short term I feel investing close to home (50 mile radius) is the best option because you have a superior advantage by knowing your market.

If you’re confident in handling the entire process from start to finish and know how to mitigate risks when things go wrong, then you probably don't need an agent.

Being boots on the ground out here, seeing the state of some of the homes here both on and off the market and knowing the price of housing in the area, I am confident that I could be successful in flipping homes here. 

It may vary from others' advice, and it will be up to you to determine what feels best for your needs.In your position, it is super smart to rent first. 

I know that my current cash flow is a result of the unit being my primary residence first, and that not all units will cash flow like this, but can't help the feeling that I should be expanding my rental portfolio over the years.

After the appreciation we have been experiencing post 2022 and what we have been witnessing the last 2+ years its hard to pick a spot and be confident on appreciation.

This means you can focus on growing your portfolio with confidence, knowing that every aspect of your investment is being handled by experts.As for my experience, I've been in the industry for over 10 years. 

Staggering when you start to scale this.Why so confident interest rates will make a meaningful drop?

Most Hard Money lenders may also require you to have the investment property under contract, in order for them to feel confident you won't try to sue them and you can pay them off either by selling or refinancing  the property you are using the cash out proceeds for.