@Zach Whitley HOT no longer needs to be factored as Airbnb and VRBO both recently began collecting each outside of an owners revenue and remits to the city on the owners behalf.Galveston now mandates this for all STRs listed on those platforms.

there are a number of factors as you previously mentioned. 

I'd pay the first round of treatments, while informing them (and have in lease) that they will be responsible for future costs of pests as motivation to keep the place clean.

Also, a factor is that to self manage (with help) is no small task.

If there are other factors I need to consider, please share those also.

Other factors to consider are the cost to refinance, any interest rate changes, etc.

The amount of loans you have won't be a factor until you hit about 10 Fannie/Freddie loans.

I would only recommend in A/B class neighborhoods otherwise guests will be turned off and you'll have environmental factors that disrupts your operations.

They’re attitude is a MASSIVELY overlooked factor people I think miss on and come in to hard on their tenants and vice versa.

As mentioned above, surrounding myself with like minded people has been such a significant factor.