A 75% cash out refi is more likely the higher scenario of the two, however when you do the refi they are paying off the total loan amount on the 12 month flip loan and netting the difference.

You may be able to capitalize on this if your area has experienced similar growth.Simplification: Selling would allow you to focus on your new single-family investment properties and potentially expand in those markets.Capital for other investments: The proceeds from selling could be used to fund other potentially higher-yielding investments, especially if you use a 1031 exchange.Small town limitations: Depending on the specific town, there may be limited growth potential compared to larger markets or more popular tourist destinations.Given the stable cash flow, low remaining debt, and your established experience with the property, keeping the fourplex seems like a solid option, especially if it's in a location with STR potential.

Commercial properties can generate higher rental income but come with higher vacancy risks and management needs.

If time is NOT important then listing at a higher price might make sense.

In fact, the median sales price of a single-family home in the Austin metro is ~52% higher than it was at the start of 2020.

Dont mind going higher deposit (down payment) rate than traditional 20%,can maybe go upto 30% as well for more favourable lending.

You won't get cash flow while you live there, but you'll have a much larger selection to offer on, giving you higher chances of finding something that's actually a deal from an ROI standpoint. 

Is there a higher chance the IRS may questions things?

-Am I screwing myself from any first time homebuyer deals, higher interest rates due to personal vs investing, etc.?

Hey @Dan DeGroffBuying as an investment property with a 0.75-1.0% higher interest rate and needing to put a minimum of 20% down (its actually 15% but the rates are so much worse at 15% that its not really an suitable option) when the home would actually be your primary residence is brutal.Partership are a bad idea 80-90% of the time, but could work out in some scenarios.