The location, the style of the home, and the long-term, cash flow opportunity.

So you can certainly have a DSCR/commercial style lender just base the loan off of the rental income to refinance it.  

I will be a remote STR host and I will need somebody to keep the yard in good shape and shovel the (occasional) snow.My HUNCH is there must be some kind of Uber/Lyft/AIRBNB-style crowdsourcing platform for these kinds of services.

Can be a lux style or plex.

Only thing I wish I would have done is use equity to expand... with the caveat of ensuring i'm not over leveraged in case of a 2008/2009 style crash.  

If it were me, I would get them leased up asap and then sell them, perform a 1031 exchange to defer taxes on any gains and buy newer townhouse style apartments that cash flow.

At this point I’m looking for ranch style homes with good roofs (none flat), furnace/AC mid life or better, brick exterior is a bonus, double pane windows, younger than 1950’s.

What is your life style? 

Oh rehab... the other investor and I were thinking a total of 75k in physical rehab to both homes, 80k for the installation of a beautiful pool area, and about 50k for the interior design on the homes.To anyone who is like WOW those are big numbers for this STR, we want to present a boutique-style stay and experience, and it's two homes.

If this plan is plausible, I want to do this for a few years to dip my toes in the water with being a landlord before trying a new REI style like flipping/multi family homes, BRRRR, etc.