I assume many people here do their own cleaning when they got started so maybe it’s well known by people who aren’t me?

I’m not sure you could really scale a STR on Shopify but you could always start there and migrate to another platform. 

I didn't have much imagination for it. 5 years ago I started looking at buying a larger home I could house hack because it allowed me to get a larger property than I could afford.

I use buildium which is a good value and I think the integration with tenant turner alone saves triple the hours needed to be worth the cost.

If you are passive in those rentals (not real estate professional for tax purposes which requires 750 hours of real estate), and your Modified Adjusted gross income is over $150,000, then the cost seg is not actually going to save you any taxes. 

If you're up for some delayed gratification and tax free cash, I think it's a fantastic idea.I would recommend starting with a paint, flooring, kitchen, and bath renovation - more of a cosmetic fixer that can still qualify for conventional financing.

I mentor a few investors especially just starting.  

May be a good start for you and you wouldn't have to sell your business. 

I'm looking to get started in wholesaling commercial real estate.

If that’s something you want to discuss, let’s connect and see if there’s a fit.This is definitely worth pursuing, but it’s all about making sure the structure is airtight before money starts moving.