Your seller is clearly an investor, and not a motivated "civilian," so that's one BIG strike against.And yes, these terms suggest he must have seen you coming: No way would I pay 44% down for 24-month financing at 10%.

You don't strike it rich overnight and building up your knowledge and portfolio little by little is the way to go.While a lot of the knowledge in BP books are great fundamentals and will help get you excited and have a basic understanding about investing, I'd encourage you to soon start reaching out and networking locally. 

That being said, I did get in touch with a Real Estate Agent in New Jersey that used them, so I know they're legit, which is when I pulled the trigger.Unfortunately for me, the person I was working with never followed through, and for me, you get three strikes with 3-day intervals.  

The problem is that realtors are not a united front so they will never strike against zillow because they need zillow as well to showcase their properties to a large group of potential buyers. 

I realize this is mostly an appreciation play and yes, we have adequate reserves if another Covid-level event strikes. 

When I expressed my skepticism to my agent, he stated the seller strikes him as a really nice older guy who doesn’t need the money (he’ll be making a bit of equity but nowhere near what he could get in the current market.)

Way to strike while the market is hot in Central FL with this one.

there is still the hope that you will strike it rich. 

Now hearing this issue perked my ears up as a potential striking point for a bargain deal, especially if I could negotiate a lender to consider the permitting issue to be covered by a 203k (possible streamline even).

Given this is an older house that won't be sellable in a not-hot market, and will likely have issues down the line relating to its age, should we strike while the iron is hot and sell now, take profits, and plan our next flip more cautiously, or should we continue renting given the stable tenant and good rents in the area?