No pricing issues but I use PriceLabs and its integration is smooth.

Given you are willing to be active, the first question is do you need a smooth $20k/month? 

Whenever you are buying a property out of state you should do a few things to ensure it's as smooth as possible.Don't buy in the roughest neighborhood in the urban core.

I'm not sure if you could make the numbers work once you tack on their fees (they have a sliding scale depending on the service you want, which in your case I assume would be the most expensive "you take the wheel" service). 

In my experience, slightly higher HOA fees can be worthwhile if they translate into a better guest experience - many travelers expect the full "resort" experience (clubhouse, pool, lazy river, water slide, etc...).

Everything seems to be running smooth.

The process is smooth, and my first property was leased out on a 2 year lease before we closed, with another that I'm working on in the same situation. 

When you're starting out, working with a real estate agent can be incredibly beneficial, as they act as your fiduciary and can help guide you through the process, finding the right properties and ensuring a smooth transaction.For repairs and remodeling, a general contractor is typically your best bet, as they can manage and oversee the entire renovation process.

Some single family homes are configured in such a way that people I know have closed the door to the house and put in a sliding glass door to the outside and rented out that room and the bathroom next to it, but that depends on the floorplan.

Seems like everything goes wrong all at once and having those reserves helps smooth things out.