Retired assets are not subject to depreciation recapture, thus enabling you to save even more on taxes.This is a list of some ways to avoid recapture:Move into the property for at least two years before selling it making it your primary residence to eliminate capital gains tax1031 Exchange: swap one investment property for another and defer capital gains taxes721 Exchange: exchange appreciated real estate property held for business or investment purposes for units in an operating partnership that will be converted into shares of the real estate investment trust (REIT)Place the property in your estate and when it passes to your heirs, they do not inherit the deferred depreciation recapture or capital gains and instead inherit it at FMVWhat are your thoughts or questions on depreciation recapture?

Commencing small enables you to acquire expertise and understand the ins and outs of being a landlord.You're already on the right track by acting; keep in mind that the initial move is frequently the most important.

This powerful approach allows investors to recycle their capital, enabling them to acquire multiple properties and generate long-term wealth.

Will be using leverage so that would mean $1m down would enable me to get a ~ $4m property(?).

I say it depends on whether you want to manage these and have an active role yourself or whether you are looking for a passive investment.If you want a passive investment, then you can look into investing via a syndication or a fund that will enable you to get the economies of scale and the location is less critical provided the sponsor has experience in that area and has a good team in place at the location. 

Get Turno to coordinate with cleaners, Pricelabs for dynamic pricing, a wifi enabled smart lock, and you're good.

That is, are there RE rental business structures that would enable this automation by outsourcing work (it's a stupid question, I know, but I just want to be sure)?

But I'm open to cost effective investment solution(s) enabling the summer/winter scenario. 

Proper screening, regular inspections, and solid policies that enable you to nip problems in the bud quickly. 

This helps take the emotions out of potential deals and enables you to see potential profit and compare deals side by side.