Is the higher price agent inflating to get the listing or is the lower price agent just not keyed in well enough in the specific neighborhood?

I'd focus on deciding what you want to do (flip-high risk, but potentially high return...or large loss; short term rental-more work, but higher return than long term rental; long term rental-less work than the other two, but lower return).Once you've decided which you want to do, then focus on getting the best house to meet your goal. 

Cost Advantage: Property prices in Mexico can be 40%-50% lower than comparable investments in the U.S. or Canada.High Occupancy Rates: The average rental occupancy rate in Tulum is 70%-80%, driven by year-round tourism.Economic Stability: Mexico's economy grew 3.1% in 2023, with a robust real estate sector supported by foreign investment.Infrastructure Investments: Developments like the Maya Train and new airports enhance connectivity, boosting property value.Feel free to reach out if you'd like more information on how to invest in Mexico, benefits and insights in general!

I can send you their contact info.Quick Tip - I would start with a range of offers (lower-end), that usually helps my clients get out of the analysis paralysis phase.

Question: Should I collateralize the loan (if using private or hard money), or rely on roll-over loans (to maximize the lower points and 3-4% rate)?

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

While you likely won’t owe taxes due to the loss, filing is still required since the rental property is located in Missouri.Kansas (KS): As a Kansas resident, report the rental loss on your KS state return (KS-40) since Kansas taxes your worldwide income, including out-of-state rental activity.Tax Impact: The rental loss reduces your federal taxable income and may lower your overall state tax liability.

Sales Tax Breaks: Construction materials and services may be subject to lower tribal sales taxes—or exempt altogether.4.

I would look at the DSCR loan as the first option.By the way, I suspect you are going to be disappointed by any refi appraisals   ADUs typically appraise poorly   JADUs can lower the property value Vs having the space as part of the primary unit.  

You'll simply sit vacant for a few months, lower the price then get a tenant.