He pivoted to STR projects, rebranded as Techvestor and since then brushed off questions about Scout pads or MBD.

Then whenever a good opportunity arises, you can simply write a check out of your credit line and purchase in cash.

Additionally, should I consider tax implications, given New York’s reputation for high taxes?

Did you put it in writing for them to have it drain into the shower? 

I'm planning to make additional payments to pay off the mortgage faster, and I'm unsure how to account for this in the ROI calculation.

Remember with a heloc, you only pay interest when and if you've withdrawn the money and once you pay it off you can use it again.

We are located in Santa Rosa Beach just off of 30A.

What are the common fears of investors who write checks to capital raisers? 

I've filled out the 1040 Schedule D Tax worksheet 3 times and each time have come back with it being taxed at the marginal rate of 32%, with no particular special treatment, based on the flow of that worksheet I don't see how it could be any other way.I have read many, many, many, many, many threads on this forum mentioning the recapture being taxed up to 25%.

This is an all-too-common mistake: a rental sits vacant, less-than-desirable tenants are approved, and then those tenants don't pay and cause issues.You have to rip the bandaid off and ask them to leave.This may sound harsh, but it's not entirely the tenant's fault.