In about a month i hit my 6 month seasoning date to be able to do the cash out refi. 

If you have a $1,500 or more spread between cash flow and living expenses, I would consider saving the rest to add to a cushion. 

Purchase price: $140K% Down: 25% (I am considering pitching the investment to a friend and making this a cash purchase - any advice regarding this decision is much appreciated!)

Ideally, my property generates around $500 per month cash flow after accounting for rent, insurance, tax, interest, PM fees.I’ve recently realized that repairs costs have notably affected my profits.

I've found some great potential PML's by reaching out to retired investors and building genuine relationships with them.

Might be a good way to get your foot in the door, not having to partner with anyone, low downpayment and a cash flowing asset. 

You can get great cash-flow in Cincinnati and I think C areas would be your best bet.

I was thinking about different ways to avoid the 6 month period in which one has to own the property for in order to refinance cash out.

Purchase price: $326,000 Cash invested: $80,000 3 bd/ 3 bath townhome, completely remodeled in 2021.

While each market - real estate and stock - has it's own risk/return profile, the comfort of owning a cash-flowing hard asset becomes more and more appealing when the stock market gets choppy.