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Sounds like you've got a good start with one STR.

I never took action and started doing deals.

Often times you will pay much more in taxes than if you pulled the money out, paid the taxes and penalty and then started investing in real estate.For example, with the financing you mentioned, the IRA must pay taxes on the portion of the profit earned by financing. 

My thoughts were that this would be a short-term solution.However, the more I think about it, I’m starting to lean toward a cash-out refinance over 25 years, with a minimum payment structure.

In January 2023, he started eviction proceedings on squatters in the home and won a judgement by default in May of 2023 and the squatters moved out.

That was right up until we started purchasing rentals.We have an LLC so we actually pay $400 per year for our LLC to file and then another $150 for us to have our personal taxes done. 

When I establish LLCs I always ask my clients to have a meeting with a CPA from the start, even if they are going to file their taxes on their own. 

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

As for finding a contractor, asking local investors for recommendations is a great start.