Spend some money to have a decent CRM or automated follow up tool in place.  2.

On my STR I have partners and it is mostly automated once you have it running but I do have to put out a fire with those every now and again.I have a great guy who is older him and his wife live on Social Security so free rent and some pocket money plus very flexible hours make it a great job for him.  

What tools/software would you suggest when pricing your STR, communicating with your guest, and overall automation?

She uses a VA for bookings, and has everything automated once the unit is set up.

Right now, already 10% of our bookings are direct and it is pretty painless and automated.

Automate the house as much as possible.

I am a huge fan of ownerreservations or OwnerRez.They have a lot of features, are reasonably priced and I have been very impressed with their customer service and tech support.I use it to manage all of my automated guest communications, electronically signed rental agreements and a lot more.

If you are going to go the PM route, I would always recommend local PM with good track record, already managing something similar to your property vs. one of the bigger providers (Evolve)You can absolutely do it on your own, just understand that you are taking on a second job which will require some work no matter how much automation you put in.  

But, it shouldn't have any bearing on what your considerations will be to help someone instrumental in helping you get closer to your financial goals.

In addition, the investment instrument that crashed the economy last time, CDO's (collateralized debt obligations) are back in the form of BTO's (Bespoke Tranche Opportunities).