IMO this is much too little additional return to put your personal residence at risk.  

I rented out the additional bedrooms to friends and family, charging them well below market, and sold when it was time for my wife and I to start our own adventures.

I rented out the additional bedrooms to friends and family, charging them well below market, and sold when it was time for my wife and I to start our own adventures.

That is in addition to clauses that require anyone that stays more than 7 nights in 12-months to apply (then it becomes our choice if they are treated as a temporary occupant or tenant) and prohibition of subleasing.

million in addition to their investors (who expect a reasonable rate of return) by keeping the rental rates at a fraction of the market rate?

A bank they actually ended up getting for free because of a tax reductions.

I would appreciate any insights and additional things I may be missing.

Keep existing and add an additional -~2000 sq feet 3.

The PMS around here are pretty terrible, I've worked with a lot of the larger ones in Cleveland and I think they just take on more properties than they can effectively handle and don't hire enough additional employees to make it work. 

For payments, tools like Stripe, PayPal, or booking software like OwnerRez work well.Happy to connect if you’d like to chat more or need additional tips!