2 tenants in this duplex 1 pays on time every month the other one pays like 5 days late for 50% of rent then pays the rest even later if I evict I would have to give a 90 day notice as they have been there for a while (this is in ny) my property manager also thinks if I evict I can get 10-20% higher on this unit (this is my first property so i don't love taking on so much risk) just not sure what the correct move is here.

I haven't personally looked, but depending on how far you consider "something nearby" you could start to look towards Bakersfield/Fresno or moving east.

I am currently in talks with Hostaway to move to their platform. 

Last time I did this STR income and expense tracking evaluation process it was overwhelming. 

I had a tenant move in last week and she sent me a video of her ceiling fan that was "wobbling" a little too much for her liking and asked if I could fix it.

I hired someone else to work on the project, and I am okay with paying him in full and just moving on to the next project.I have already paid him ~300k, and ~40k of the last payment is remaining.

processing fee being wired for LOI is usually code for a fake lender or a lender that very well may never fund.. so caution on that one..

If my cleaners arrive before the guests leave, they have instructions to knock on the door and get the guests moving along.

Unless my thought process is completely wrong.

Trouble is that I don't yet have long-term employment in place (just moved to the area a month ago).