My #1 headache is cleaners. 

One that works with RE professionals. 1) YOU get a much cleaner, crisper look at all your numbers when you need them.

I'm leaning towards Baselane because of the UI is way cleaner but they don't have a mobile app which doesn't help me with receipt uploading on the go...

@Benjamin Papet if viable to have STR, I’d would underwrite with more wear and tear and get good cleaners.

What you need locally are cleaners and handymen. 

In looking through Bigger Pockets & other resources on the web; it appears this estimator is attempting to take me to the cleaners, but I'd love to hear from any of you who have more experience with this sort of thing. 

Without using this forum to get into every detail, the basis of him getting an OOS deal was to find someone local where he wanted to invest and use the team I have built (realtor, cleaner, maintenance, etc.)  

I also auto schedule cleaners through my software when any booking comes in. 

I have a Rockstar house cleaner that does it for free, and I get to sleep with her. 

It helps avoiding voiding the title warranty and also keeps the title chain cleaner.