Picking a house with major, costly structural issues or in a location with poor rental demand can hurt both the rental and refinance phases.

I'd like to pick a good platform and keep everything under one roof - not need multiple tools. 

Try to pick a strategy that you can be passionate about and of course makes sense.

If you had to pick one state with the highest change of exploding insurance premiums over what they are now, other than maybe CA, it's Florida.

I will be there the following morning to pick up the keys and complete the move-out inspection."

If the property is on a boundary or near the edge of a neighborhood you may need to pull the comps within a mile and then pick out the ones in the same neighborhood as the subject property within a reasonable distance.

Buildium, Appfolio, or Yardi are some ones to pick from. 

Historically cleaning fee's reflected pre-Airbnb the  way that Mom and Pop joints allowed customers to pick if they would clean up the cabin or if the resort did. 

Unfortunately as good as TurboTax and other online softwares are, they don't always pick up the most beneficial items with rentals.

I looked at various tools but ultimately picked Baselane due to its ease of use and scalability.