@Jacklyn Robins not trying to be difficult, but how many Class C or D properties do you have besides this one?

Licensed with permits ~$3,250.HWT standard gas single family low efficiency without exhaust retrofit $900.Sand and stain hardwood floors, natural stain $3 per sf.Paint interior walls, ceiling trim and doors 3 tone paint scheme 2 coats $3.20 per sf (floor area cost includes paint)Click lock LVT flooring install overlay inclusive of prep and quarter round $4.50 per sf (materials and labor)Asphalt roof installation 3/1 - 800 sf bungalow with 2 layers of shingles - ~$7,900Standard porch cap replacement with 2 new precast concrete steps ~$2,500Used stove or refrigerator delivery and install $350New stove or refrigerator delivery and install $HD model specificUse this as a general guideline. 

If they are difficult, the current landlord may not give you a straight answer because they want them to find a place and move out.

The island is not that large so if you target a specific location you like Im sure it wont be too difficult to get to know the ins and outs.

It sounds like you are off to a great start for 2025 and have a good plan.Finding good deals is often the most difficult part of the process. 

Our property manager has said Portsmouth is a difficult area and we are going through a slow time now.

What is the cap rate?

Now this property is in a class C neighborhood with a calculated 11% cap rate estimated.

CA is an expensive market and regarding tenant laws in my eyes more complicated/difficult as a rookie landlord.

I imagine refinancing option 2 would be more difficult due to the higher LTV.