The tenant has a history of being bad with communication, but I'm getting concerned given the circumstances. 

There was no communication and explanation what was happening and why, but simply asking for access to the properties for appraisal. 

Outlining your expectations for your tenants (and communicating those expectations well) will save you a lot of trouble down the line.A common mistake for first-time landlords is to be overly lenient, especially when it comes to on-time payments.

I found the deal in a super hot area of town and helped my mentor Logan with any and all communication and execution items needed to get the deal across the finish line.

Great communication.

It doesn’t make sense for them to come out and give you 10 estimates if your not going to work with them.Always visit a current work site, make sure they communicate, respond quickly, and you get along with them.

Do they have a communication plan?

Continue as normal, no special communications and let the tenant transition to a month to month lease.

These properties are not under contract by me - is it bad for me to put the buyer in direct communication with the contract holder, or should I "gate keep" all conversations? 

They dont always communicate between the lender and underwriting and they will go ahead and just run your credit and then you have to explain something theyve heard 100 times "No I usually have an above a 800 credit score its just because they ran my credit without asking"Create a dropbox or gmail account specifically for the properties where you can store all the important documents.If you are doing investing and have full time job, good luck and godspeed, this became a second full time job and I ended up losing a long time girlfriend over it.St.