@Matthew Crivelli  HUD Section 8 does not pay above market rents. 

I want to pay a Monroe County realtor to go through the various areas covered in the list of properties and give me their thoughts about what areas to focus on.

I buy my STR's for fun so that I have cool places I want to go to for my family that pay for themselves and make some money.

Most flat fee listings are willing to work with a buyer's agent and pay the buyer's agent commission.

.- If I pay property taxes online (let's say with a credit card), will my name show up as the payor or will the trust/trustee's? 

Option 2: We pay cash to build a small 2/2 cabin initially.

See the illustration below (click to enlarge).Goals“If you don’t know where you are going, you might wind up someplace else.”

I always am amazed when someone selling a $600,000 house brings me a listing agreement where they agreed to pay a stranger $30,000 to list their house for sale and they didn't even read the agreement much less spend the $250 to have a lawyer tell them that yes, if they sell it to their cousin during the listing period they still have to pay the $30k.

., Purchase Price: $475,000 ($197.9/sq. ft.).Estimated Market Value: $402,000 ($168/sq. ft.).Financing Terms: 2% interest rate, with a 9-year balloon.Unit B Income: $2,049/month (Section 8 tenant through November 2025).Unit A Income Potential: Similar rent or higher; Section 8 cap for the area is $3,234/month.Monthly Loan Payment (P+I): $1,386.Cash Flow Breakdown (if both units are rented at $2,049/month):Gross Rent: $4,098/month.Vacancy (10%): $410/month.Operating Expenses (37.3%): $1,376/month.Net Cash Flow: $943/month.Key QuestionsWould you be comfortable paying an 18% premium for financing at 2%, especially in a market where current mortgage rates are closer to 7%?

Your paying $180 for nothing for now.