I equated it to a property per year simply because in the Denver area it's very difficult to find cash-flowing deals that make the investment worth it, so I figured I'd be looking at several properties to reach my financial goal. 

So I'd be doing my best to get the highest possible rent/revenue but without needing or counting on that.What you refer as cut-throat competition exists in every market where you have demand.

Then, run a rental stress test on the new STR assuming a worst-case scenario—like converting it to a long-term rental with a 30% cut in future rents.

The agent will have access to the biggest platform to get the property sold though, the MLS, so forgoing even a cut rate agent will create more of a loss than the agent fees themselves. 

As of my last update in April 2023, the definition of an accredited investor includes, but is not limited to, the following:Income: Individuals who have had an income of more than $200,000 (or $300,000 together with a spouse) for the past two years and expect the same for the current year.Net Worth: Individuals with a net worth exceeding $1 million, either alone or together with a spouse, excluding the value of the person's primary residence.Insiders: Directors, executive officers, and general partners of the company selling the securities.Professional Experience: Certain professional certifications, designations, or credentials or other credentials issued by an accredited educational institution may allow an individual to be considered accredited.Knowledgeable Employees: In the case of private funds, "knowledgeable employees" of the fund are also considered accredited investors.Institutions: Banks, partnerships, corporations, nonprofits, and trusts with assets exceeding $5 million.By imposing these criteria, Regulation D is meant to ensure that all participants in such an offering are capable of fending for themselves or sustaining the risk of loss, thus requiring less regulatory protection.Under Rule 506(c), it is not enough for an investor to simply claim accredited status.

Most investors focus on what can they buy now with their available capital instead of simply what is the best investment for their capital without limitations. 

@Chris Johansen I believe the part you're missing is you are not "simply loaning him money" under the new iteration of your partnership arrangement.

As long as you specify the bank name, address, and interest rate in the lease, you're meeting the legal requirements.To avoid the hassle of having to have the tenant sign the lease twice, you can simply leave the account number blank in the lease and note that the deposit will be held in a specific account at a designated bank.

Most simply, let's assume you do a cash out refi for $336K and the interest rate is 7.00%.

A 1,000 sq ft cabin when you have 300k into the lot just won't cut it.