However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

I'm looking for the cleanest & most visible way to access payment history, see amortization schedule, tax documents, etc- much like bank softwares provide. 

If you don’t have access to title company services, go to Norwalk recorder’s office and “chain” out the ownership and open mortgages.

Generally the thing that keeps commercial/industrial investors afloat is access to large sums of money to survive a downturn.It sounds more like this property is an outlier in your wheelhouse and portfoliio. 

It's also located near many other State Parks, Nature Preserves and Forests giving access to a lot of good hiking. 

Right now I am considering doing a cash our refinance on both to access the equity.  

This allows you to access funds while keeping your existing mortgages intact.Second Mortgage: Explore lenders who offer second-position loans on investment properties, though rates will be higher.Cash-Out HELOC : While traditional banks often restrict HELOCs on non-owner-occupied properties, some portfolio or private lenders may offer HELOCs for investors.With $15-20K in liquid funds, look for deals where you can negotiate terms:Seller Financing: Negotiate lower down payments or interest-only periods.Subject-To Financing: Assume the seller’s existing mortgage while covering the down payment.Lease-to-Own: Lock in the purchase price while using rental income to build equity.

I’m looking to expand my network and connect with other investors, realtors, and real estate professionals—especially those who are growth and collaboration-oriented.

Canada has credit reports similar to USA.Google to see if they have a version of TransUnion that can be used to access.

Lastly, your investor agent should have access to off-market, pocket listings, fsbo, and many more deals that you can't find on-market!