The downpayment and closing costs would be one large hurdle in order to repeat this, I'm not sure how willing lenders are to allow 3 properties a year.

As with all regions, the Oregon Coasts' counties and cities are tightening their rules (and quantities of allowable vacation rentals) and there are a few adjustments to last year's regulatory landscape.

They have to allow them in to inspect to make sure things are copacetic.

If you don't plan on allowing 4+ cats in your rental in the future you shouldn't start now.

Quote from @Jemini Leckie: Hello, I am trying to understand the Orem, city code to determine if I am allowed to rent my basement ADU that I currently live in two a couple cousins and their friend.

That will allow you to build the additional legal space further amplifying the value of the proprety (more HELOC money). 

None of those types of loans allow LLCs, therefore, that lawyer is incorrect.

It also identifies signer names within the documents, allowing you to uncover the owners behind the ownership entities.Currently, lenders primarily utilize the platform to monitor client and bank activity, but we're exploring options to tailor the tools for investors.

After some research online, I am reading that the cost per square foot on a gut renovation of this nature in Stamford CT is anywhere from $150-$350, which is ultimately not very helpful, because at $150 per sq ft, this is a very appealing project with a total profit of ~$175K (46% ROI) and at $350 per sq ft, it very much isn't, because it would be a net loss of 83K (haha).QUESTIONS:What can I do refine my estimate a bit given that I am not allowed to a formal inspection on the property? 

I don't know a single broker who would allow an agent to wholesale while hanging their license at their firm.