Quote from @Tod DuBois: Hostaway appears to integrate with the multiple channels - but I hate to do a software setup and learn it's not a good place to do what I need to get done (which is work as little as possible and optimize my occupancy).

As it relates to lease end dates I've seen two things work here. 1) You can stagger end dates as mentioned above or 2) you can optimize for summer - this works better for us in areas where you see students or families with school age children moving to align with the summmer months.Separately, this is a great argument against month-to-month leases.  

Still there's more risk than a house hack which is probably your optimal strategy.

If you need tailored funding, we can help optimize your financing.

Second, for you as a taxpayer you need to evaluate if your tax situation (e.g. property type, tax profile, material participation, etc.) will allow you to leverage additional losses generate from cost seg to optimize your taxes. 

To scale, replicate this winning formula in similar markets, optimize operations for Section 8 tenants, and consider networking with like-minded investors to uncover new opportunities and partnerships.

We are excited to announce a new Pro Partner - Stessa - who helps investors manage and optimize their portfolios.

The value add was recognizing what the current regulations could allow the land to be used for (basically recognizing current land use did not optimize the value).Good luck

Does this matter if you're not optimizing for building a ton of wealth to pass onto kids? 

I would stop short of saying I found the inflection point of optimality and being pragmatic.