You are mention the higher costs for MTR-- I would adjust the cleaning fee and add incidental insurance like Waivo to cover those costs.

I was actually on a team dispatched to investigate the Surfside Condo collapse until the clean up process basically rendered our investigation moot. 

It felt like a no-brainer for the value of the land, but being able to utilize a traditional mortgage because there was a clean yet simple 3 bed 2 bath house on the lot made the deal even sweeter!

Guest checks out, cleaners arrive to clean, conduct post stay inspection, and reset the home for next guest.

This would not be something a roofer would do.I'd look to see if there were any work orders for cleaning debris off the roof or for clogged downspouts. 

I currently have  1 Business Bank Account that is for Master LLC and stuck on best way to manage cash flow  and flow of funds between account for all master expenses related to my business setup vs and also expenses/ rent related to the properties to ensure that I keep things clean, simple and easy for reporting, taxes.  

It's usually cleaning, re-painting, furniture removal, etc.

My question is, he's been clean for the past 15 years no criminal record before or after that incident, has now a fiance and has been living with her and her 2 children for the past 5 years, has a good income and good credit.

The more complicated your business structure becomes, the more problems it can actually cause such as when looking for lending options, getting the best interest rate, keeping clean accounting, filing taxes, opening bank accounts, getting credit cards, executing a 1031, making title insurance claims or even triggering a due on sale clause, etc. 

After all PITI, utility, and services (lawncare and cleaning) costs I have $7,225.I set aside 25% of this for my maintenance fund.The remainder funds my lifestyle, wife has a Tesla, and quarterly vacations as well as business growth.In 2023 I am tracking to build 4 duplex units designed as room rentals funded in part from a recent land sale.