$300-$400k will likely not get you even a 2-family in the best area of New Haven unless it needs a lot of work, but will get you a property in a top flight area of Hartford.

I’m also open to alternative strategies, such as private lending or passive investments in funds, to diversify and balance risk.Does this phased approach seem reasonable given the higher HELOC rate?

The investors I have worked with have found it to be a lot easier with the updated technology and everything going through a massive change post covid/2020. 

Oklahoma as a whole has strong rental demand in many markets, just need to be mindful of the price-to-rent balance, as you mentioned.

I'm not a tax expert, but I work with them.

If you are new, it will take you a year to recover from a 1-star review.I have been staying in timeshares and short-term rentals my whole life.

I’ll try to keep this as short as possible but I am at a cross road in life here and can’t seem to find the guidance I need. 

I have found ChatGPT to be particularly useful for testing new Book Covers for BiggerPockets, such as our foray into the personal fitness category with upcoming title "Sweat for Life": 

In theory they've tried all they can and are stuck on stupid feeling there life is about to be burnt to the ground. 

You need to work with someone whose proactive and will send you on-market, off-market, and pocket listings!