I currently have 8 doors all producing positive cashflow, spread out over three different states. 

My question is am I going to have trouble finding a tenant in the last months of the year such as the holiday months or should I wait till January for example?

I can remember when it took on average, 180 days to sell a house***************************************************https://www.dailymail.co.uk/real-estate/article-15086063/big...Housing markets across the US are showing signs of trouble as properties linger on the market in 44 out of 50 major US metros.The worst hit area is Miami, where houses are now sitting unsold for nearly three months — almost four weeks longer than a year ago.Across the country, the typical home spent 60 days on the market in August, seven days longer than a year ago and above pre-pandemic norms, according to a Realtor.com report.

Such actions are wholly unacceptable and should not be tolerated within any professional environment.The discrepancies between the program's marketing claims and the actual conduct of its top students, as exemplified by Kristin Witherspoon, are deeply troubling.

Many of these places that look like good deals are full of trouble tenants. 

If that same person comes back to us after not accepting a quote and wants a second quote, we bill a high number up front for producing a quote.You are up against contractors that already have a full pipeline of high value work, and do not need to take on high risk clients, who may or may not be able to pay, and may or may not know what they are doing.  

Our best suggestions for hiring cleaners are...(1) Find and hire experienced turnover cleaners with a verifiable history of consistently producing 5-star reviews for cleanliness (the only part of the review they can affect).(2)  Ask for referrals and call them. 

If you went without "anything", I think you'd have trouble with sealing the bottom of the door with the foyer if you were looking for something without a dedicated threshold. 

I am in the process of purchasing a sober living house but am having trouble finding an insurer that will write a policy on the house since it is being used for sober living. 

As you may find that alternative more trouble than it is worth, here is a simpler alternative:Only speaking as to CA (but likely in most other states), if you obtain an "abstract of judgment" from the court (for a fee) and record that abstract of judgment at one or more County Recorders (for a fee), the credit agencies will pick that judgment up and report it on the tenant's credit report.