But now I'd like to give it a try myself!

The only problem I now see is that I got sidetracked from my plan and now I'd like to pivot and adjust my routine to my interests and become the investor friendly agent, helping new and existing investors get their first or next investment.

I feel like I get laminated post cards from multiple sources/industries almost every day and I just toss them without more than a glance.

Currently I have a mortage and it seems like a lot of work, if I have to change the deed.

It sounds like you’re aiming to offset your W-2 income with potential real estate losses, which can be tricky if you don’t qualify as a Real Estate Professional.To qualify as a Real Estate Professional, you or your spouse need to spend more than 50% of your working hours and at least 750 hours annually on real estate activities.

But otherwise I like the extended stay biz plan!

They will likely have an edge over you due to their local expertise, relationships and physical presence. 

Re-leasing is likely a month rent, plus whatever painting/repairs you do.Not sure if this is a "good deal" yet as it would depend on your proforma and projections after you consider the above.

What did you like/not like about Hospitable that made you consider the change?

People post properties like you mentioned all day long.