Recently my duplex’s property value was reassessed and my taxes went up almost 3x what they once were (bc it was assessed pre-flip before my purchase) so my Escrow shortage is about 4k.

Makes me wonder if someone has a great pre-purchase checklist they use for their due-diligence, at least on SFH purchases?

I'm assuming you're talking $110k cash and not an amount you'd be pre-approved for?

If you make certain your buyer is pre approved, the documents line up, and you keep good communication, the selling side has never proven to be difficult to me.With that said I agree with @Rick Santasiere in regards to scaling up.

My family and I are looking to move between January- April of 2025 and we bought our current house pre 2020 so we have a large chunk of money in equity, we really have 3 options on our plate.

If you are looking at protecting your profit, you can have a prepayment penalty, that would be graduated, for instance, you could have a $50,000 prepay year 1, then $45,000 year 2 and so on until you get to year 10 with no pre payment penalty.Also for future reference you can get Fix and Flip loans without having to tap into the equity in your primary residence.

Using the 50% rule (taxes, insurance, Capex, maintenance, vacancies, property-management), that should give us ~19K/month in pre-tax profits that achieves our 10k/month financial goal after-tax and adjusting for inflation.Our assumption is that building new-construction would reduce capex & maintenance the first few years. 

The fact it was purchased for $150K just effects how quickly I’ll have enough equity to make a cash out refi worth doing.Your index funds are pre-capital gains (assuming they aren’t tax advantaged) which mean’s you’ll probably owe 15% on returns.

As I have indicated multiple times, pre q2 2022 you could obtain modest cash flow on the cheap Midwest properties.  

The only thing they have is a list of current properties which are on the upset bid period, and then just a billboard of documents scattered around showing properties which are in pre-foreclosures.