Property management (outsource some responsibility). 

I have no problem making calls myself but have outsourced this because my "day job" schedule can be rough.I do agree with @Michael Orlando in that doing it yourself can be best depending on your goals.

Reasons I like STR over LTR:* No landlord/tenant relationship, no evictions* Higher returns* Weekly professional cleaning* Weekly review of property condition* Weekly repairs/maintenance performed* I can visit the property whenever I feel like or need to by simply reserving a few days on the calendar* Easier to raise rental rates, can react to market conditions more quickly than if locked into a long term lease* Just as easy to outsource to a PM as a LTR, or not, in the right locations* Easy to purchase in locations you want to visitGovernment in many areas (all if you consider CDC mandates) treats landlords as the enemy, why fight them when they hold all the cards?

"BEST CITIES" is going to be relative to you in a lot of ways; do you want to be hands on or outsource management?

Still, I plan to for the first few months as I fine tune things, but very quickly it needs to be outsourced. 

Or outsource this task to an actual bookkeeper and keep my energy focused on other aspects of the business?

If you do the passive route, you are outsourcing all the decisions.

You could outsource this data entry or convert the owner statement to a spreadsheet and batch import. 

The only item I outsourced was electrical updates ($2,100 to remove knob and tube and update everything to current code).

In Racine Co they outsource their inspections, in Manitowoc Co they still do the inspections in-house.