A $240k loan amount on a $249k purchase price seems crazy and I'd never expect to produce any net positive cash flow doing this.How are you calculating your property taxes?

Many banks securitize their loans (bundle them together) and sell the loans to Fannie Mae or Freddie Mac, while continuing to service the loans, that is collect your payment.

it will be a corporate/wellness retreat/short term rental destinationI need land that is close to the Action, but not too close, and preferably comes with two single family doors already built, so I can take advantage of Fannie Mae owner occupied loan and develop the rest of the land on my own and with private funding.Is Columbus a good market for this strategy?

He is very good about deductions on tax returns so his income looks negligible and of course banks wont talk to him about loans.

Unless it’s specified by your loan type or lender, you don’t have to.

Also, did you have any other loans (ie student loans, primary residence mortgage, etc) when you took on the $25k? 

HELOCs are not available because they are residential loans guaranteed by individuals and what you seek is a type of commercial loan or credit line which are available to seasoned companies with proven financial track record.

These properties can provide cash flow and diversification while qualifying for favorable residential loans.

People reinstate the loans and do loan modifications all the time.

You could use a HELOC, but with VA loans you have an allotment so you can get loans on more than one home depending on how much bandwidth they give you.