How do you handle it?

I saw a prior post where you mentioned having a STR in Texas.you want to have a conversation with your accountant to see if it can be treated as an active property instead of passive.If it can be, then there is a potential opportunity to offset the losses against other forms of income such as wages, interest and dividends.

Do you think it is best to first max out Roth IRA before investing in real estate?

There are plenty of possibilites there, it's a huge state.

Honestly there are several career paths that will help (Renovation contractor, real estate agent, corporate RE analyst)  but depending upon whether you are looking for a career investing/flipping versus using your W-2 career income to build more by flipping, you can approach it better in my opinion by learning through doing.Flipping especially 1 at a time isn't a full time job and my thought is that you get help on your first, maybe first few flips. 

I also own a couple in Memphis so it’s interesting @Dirk Singleton that you’re moving away from TN.

They should be doing a load calculation, taking into account insulation and window type if I'm recalling how it works properly. 

Those that have these investments--with minimal lease terms--do you have problems getting tenants?

Has anyone ever applied for an sba7 small business loan and applied it to one or more rental properties.

I am not in the space I do have a few MF investments in syndication as well..