This person IS the stereotypical condo HOA board member and the #1 reason why I think condos are one of the worst investments; right behind mobile homes in senior parks. 

This is so silly that you have to structure your addresses in a way to work around underwriter stereotyping such as moving into an apartment first (any other address, parents, aunt's, apartment, etc) , renting out the SFR for full 6 months prior to reappying for a FHA loan (6 months is a general time frame many underwriters are comfortable with but not a black and white rule).Your lender should be able to help you bob and weave through these two hurdles above pretty seamlessly.

You'll end up a perpetual looker -- never a buyer

The neighborhood is in North Charleston which has an overall stereotype of being a little low end, although there are many parts of it being gentrified.

I'm interested in using the cash to help purchase BRRRR properties, which if done properly would return my initial investment, which I could use to pay off the HELOC, but I would be locked in perpetuity (albeit at a lower rate) if I refi.  

I have 5 acres, which is not enough to qualify, so now I eat an extra $3,000/year in perpetuity.

We can talk about this in perpetuity but the fact remains that we don't know these people so they don't deserve to be insulted in any way.

I work in tech and worry that I fit the Silicon Vally stereotype too neatly (chia breakfast pudding followed by a drive in the electric car to yoga???)

I'm surprised that the tower revenue is so low, but regardless, they're asking you to buy and pay taxes 100 acres, but to let the tower company use a chunk of it in perpetuity, while the seller earns the revenue it produces.  

Humans generally are quite good at stereotyping.