Originally posted by @Scott L.

Quote from @Nicholas L.: @Dan Tranjust curious - why is this your goal? 

A "reorganization took place, one of the families left the group in exchange for the insurance proceeds and the property then had 4 owners (and 4 cottages)2000:  I bought ($42,000) my parent's share.2000-2010:  I bought the other shareholder's shares (total $300,000), leaving just me as the sole shareholder2017:  Elected to file as S corp.None of these transactions were properly recorded.2022 1120S tax return (2023 is on extension) shows:$0 income$15,000 Land (sched L, line 12)$122k Loans from me($189K) Retained earning$93K cap stock($46k) Sched m-2I have no idea how we got to these amounts.Does any of this make things easier to understand and easier to get me out of this capital gains problem (or does it just muddy things even more)?

I agree with @Nicholas L. that you should simplify your strategy.

Quote from @MATT L CLEMENTS: Quote from @Brett Adler: Quote from @Rivers Fike: Have not heard of them.  

JPMorgan Chase, Nationwide, Honda, L Brands, Huntington, and Amazon are just a few of the many companies that have thousands of jobs in the city.

I just started an application with Bank of America, which is where I do my banking, but damn, they want a complete application with records on all six of my properties, P&L statements, insurance riders, and the whole nine yards. 

@Taylor L. in the midwest, my partner also covers the southeast. 

Quote from @Nicholas L.: @Benjamin SulkaI think it's fine to present your analysis, but you can't "convince" anyone of anything. 

You may also be better off looking in some less expensive markets in ME like Augusta or L/A for these types of deals since your downpayment will stretch a little farther.