We tried offering seller financing, money toward buying down someones rate, etc.

All offers to buy/sell should be posted in the Real Estate Classifieds.

Sorry to not offer a connection, but for this one I think your best bet is to find the "land specialist" realtor in the area and get a CMA.If you want an extremely precise number hiring an appraiser is most likely the move. 

I recently read in a book that suggested I should open a dual checking and savings account, and take the security deposits from my future tenants and store them in the savings account, then use the checking to pay the mortgage or maintenance fees.

"for rent by owner", investors)-search for non-homestead properties in your county and send postcards to those owners that own homes that meet the criteria you want to focus on-network with real estate attorneys -network with trustees in banks that offer trustee services-look up court records of landlords who have filed their own evictions and send them postcards -network with HOAs that have non-homestead properties in that association -when you see a "for rent by owner" sign in your area, send the owner a letter -join Facebook groups (for rent by owner, landlords) and being to contribute -improve your SEO on your website-find someone who can help you gather landlord info from Zillow, etc.

This separation helps in maintaining clear financial records and simplifies tax reporting and financial management.Setting up an escrow account specifically for rental income within your LLC can offer several benefits:Financial Clarity: It separates rent payments from other operational expenses, making it easier to track income and expenses related to the rental property.Legal and Compliance: Helps in demonstrating that rental income is kept distinct from personal or other business funds, which can be important for legal and tax compliance purposes.Tenant Transparency: It provides transparency to tenants and other stakeholders regarding where rental payments are deposited and how they are managed.While it may not be a legal requirement in all cases, maintaining an escrow account specifically for rental income is a prudent practice that many experienced investors and landlords follow.

I would just suggest to keep things simple "overpay" for the property and just treat it all as basis in the property. 

About to make an offer. 

Not Detroit, Cleveland, or some of the cities you've suggested. 

Some studies suggest that cities with an increased STR availability only drive tourism by 2%-4%.