I think the actual settings will vary if you are managing directly on platform or using third party softwares, etc.As mentioned above I think risking going vacant over a major holiday will outweight the extra housekeeping cost.Also, I am not sure how much volume you are doing but do not pay cleaners extra for holidays. 

My real estate agent handled that for me and I think it's very good to confirm the rent amount and security deposit.

Hey everyone - Wanted to confirm something before filing the taxes for my STR, which is located in Virginia.Am I able to deduct all insurance, taxes, and mortgage interest for the year if my STR was available for rent the entire year but only had renters in it for 150 nights?

You posted the raw data, just go one layer deeper to get to % returns to confirm your purchase price in relation to your expected return/profit/cashflow:$5,500 + $3,000 = $8,500/mo or $102k/yr GOI (gross annual rent collected)Knock off 25% for expenses and you are at $71k/yr or $5.9k/mo NOI on this $1.05M investment or holding this at a 6.8% cap rateWith your 7%, 75% LTV loan, you'd be paying $5k/mo for the loan, leaving you with $900/mo or $10.8k/yr in Cashflow.Now to determine your CoC return (Cash-on-Cash), take the $10.8k in CF and divide it by your equity-in, likely ~$300k, so 3.6% return on your cash/equity in this deal.

Talk to some local PMs as wellIf your analysis confirms their recommendation you may have found a winner. 

I would first confirm that your HOA allows rentals, specifically the terms that they allow, or any other rental restrictions that may need to be followed.

Batch Leads - To be fair, I tried BL really early on, and it's possible that I didn't know what I was even doing but I strongly believe that software should be scalable.   

Per the original issue, circling back to confirm that I connected with a lawyer I've used before and they suggested to just issue a standard termination of month to month tenancy which requires 30 days.

Confirm with a tax pro.

I assume that by "charge" you mean assigning expenses within your expense tracking software.