I also own a small STR property management company and own two STRs out of town that I operate remotely.

I have found that multifamily properties tend to cash flow better than the single family homes. 

I realizing the duplex conversion strategy is more complex I probably wouldn't try it on my first property, just want to get a sense of what's possible in the Chattanooga market :) Thanks!

If not, I most definitely would reach out to the tenant, introduce myself and ask if they are going to be out by the 31st or the 1st, I would communicate  to the tenant as if I know they were told they are expected to leave, otherwise you may find they "do not know" they need to leave even if they actually know they need to leave....In the case they claim they are not aware they need to leave, you would need to follow the laws in the state you purchased the property, usually you can find that info on the states judicial branch or speak with a landlord tenant attorney. 

The property will be under both of our names, so the longer we keep it, the longer it will be both of ours!

This could make or break the marketing of the property.

Curious what types of properties you are looking into? 

I have a property on the barrier island that I do not want to list on MLS but I am interested in connecting with realtors or investors who typically sell or buy pocket listings and may be interested in this property.

Once complete, they will assign the property to me.

We placed our biggest bet on a single property, class B shares.