It will be simply are you able to demonstrate an investment intent.So what a great way to pull tax free cash out while still deferring the rest of that profit. 

The wholesaler who is too unknowledgeable or incompetent to ever conclude a successful sale and costs the seller precious time by tying up the property in a contract that won’t ever close4.

As @Tarik Turner referenced, the other way that some lenders allow for STR properties is by simply diverting all STR-use properties into their "No DSCR" Programs.

Also see if you can transfer your property tax basis.If you don’t sell, your insurance costs will eventually climb to 1-2k/month which simply isn’t worth it imo.

No, I believe depreciation recapture simply gets added to your ordinary income, and then taxed accordingly (Max 25% for the recapture).

@Aaron Vargas You simply setup a bank account for each property to track the rents and expenses for the property and distribute the excess when you want. 

What would stop you from simply managing the STR yourself?

It is simply more risk for more reward.  

I have looked into property radar... and most properties simply list an LLC and a mailing address.

Any contracting business large enough to do this would simply do it themselves .