It's not feasible for everyone but if you can swing it it'd work out 

2) What workarounds should I be aware of in any of these platforms to handle "routine" property management with units?

For us we either do or do not provide and if it’s provided then we as the owner are responsible for routine maintenance on the appliance and only time tenant is responsible is if they did not take proper care (or use) of the appliance.as a sidenote what if a tenant said - cool not part of lease come remove it I want my own fridge - you will spend more moving it out than you would by including it in lease. 

Just hoping it will all work out.

In the real estate investment field long enough, we all have losing investments; those that don’t work out as planned, and those that approach the “disaster” state.  

Good morning GP, If your property sells for $300,000, your "net sale price" after deducting your routine selling expenses (brokers commission, title, escrow, closing attorney, documentary transfer tax, etc.) will likely be around $275,000 (ish). 

In either case, you have to pay up to 25% on the 1250 depreciation recapture for any rental property and CG on the portion of the proceeds proportionate to the amount of time it was used as an investment, sooooo...things would be complicated and the savings on the second unit may not work out being that great.

We do not lend on STRs and we routinely refer folks to Mark at Visio. 

Like Michael said, I would use a cleaner once a month to clean or biweekly, restock the common area items (like TP, dish soap, etc), and sign up for routine lawn and snow services.

As a private lender myself, this is something we routinely fund in my markets because of this lower asset levels.