Conversely, someone with a smaller portfolio might have a WIDE variety of experiences and expertise in a lot of areas because they are hands-on in all aspects of investing and could give you guidance you can employ in ways that suit you best.

While the wealth of knowledge and experience on BiggerPockets is wide and deep, I would not trust a decision like this to the internet, I would ask you CPA and if you do not have one find one who specializes in this sort of thing.

That being said, I have detailed measurements and pictures of every angle inside every room, and to me that’s worth more than seeing a place in person since I do plenty remote renovations.

While the self-directed IRA is a great structure for investing into real estate and other alternative assets, the Solo 401k is widely considered to be even better.Compared to an IRA, Solo 401k contribution limits are roughly ten times higher and there is no custodial requirement for the 401k.

I think one angle to consider is instead of learning how to manage, learn how to own and then adapt that to become a co-host.Something like owners work/hire you to pick up slack in regards to being a "on the ground" person to handle problems.

The door opens wide open for tax strategy then.Good luck!

In that case, I see the angle. 

An HOA is a widely used form of community popularized by the developer.  

I would not trust an average number.This will be very specific to your management, your lease, your leased property, the area etc.Some people have made money, but I've not heard much about arbitrage lately, and some have lost money and  not honored their lease.In general this is just a job and not an investment, so it's widely discouraged in this forum.

Vermont is also considering a state wide occupancy requirement for STR operators which, if passed, would decimate the market.