My statewide and generic keyword rankings have steadily been going up.

Days on Market is increasing steadily, driven by those older condos. 

Fear of what I don’t know about RE investing and making mistakes was definitely holding me back, but now, another issue has risen- the actual pain of dealing with tenants and trying to learn property management on the go, and it is holding me back a bit from adding another property.

Rates are hight right now and if your primary residents has a great rate the HELOC normally is the smarter play as long as your have repayment plan that allows you to risen and repeat.  

My most recent was insured through Steadily and they used Foremost.

For us it varies by market but in our primary market 15% plus a small monthly fee to help cover software costs etc if it's a lower gross property.That's full service, host doesn't have to worry about anything and can forget the property even exists if they want to.We do have tiered services where it's 10% (w/ no or lower monthly fee) if the owner wants us to only do one side of it (either manage bookings but not guests/cleanings/maintenance, or vice versa).25-30% used to be more normal but that's legacy pricing now, for a couple of reasons.1) Of course margins are much thinner for owners now that revenue has generally come down across the board from the peak, while home prices and interest rates have risen alongside that.2) Probably even more important, a simple supply/demand equation, particular to the case of increased supply. 

Rents and prices are steadily going up and they are continuing to build. 

I am thinking if this works maybe I try this model in my market.. since our average prices have risen to 400k or more.

Have you looked at Steadily?

Oh wow USAA - that is cool, let me know how that works out.Did you try Steadily?