This shows me your version of 'financially healthy' is normal, as in the same tired vanilla ways generations past have kept themselves working for someone else for 50 years. 

They are the largest demographic segment we have (about a quarter of the population) and they are new to the real estate market, but their are tired of paying rent (the oldest millennials are now 38) and make 40% of our buyers.

Rentredi reviews there give me pause....)Also with screening tenants, we are evicting a hoarder so I would like to make some of that online and not having people do manual applications, did I mention I live in Long Island and go to NJ 1-2 x a month to collect the rents and meet with our aging bookeeper who is tired after faithfully helping my parents for 13 years.Review sites (landlord guru, getapp have mentioned Rentredi,  Rentec Direct, TurboTenant, Hemlane.....I have a sales call into Rent Manager, from what they say it would be $200 a month but we gross $14k if everyone pays so that would be a little over 1%. 

I suggest looking for owner financing for the new property, tired landlord situation is probably ideal. 

Too much risk that STRs will just go away.Honestly I am getting a bit tired of these kind of "guides".

I know you're probably tired of reading at this point...I think it took me a year to get my first two page post!

We’ve got some learning to do but I want to buy something to get real experience and I’m tired of renting apartments.

Old and tired with good bones?

Especially at chopping up tired/retiring investors portfolio and repositioning properties as BRRRRs or flips.

I was tired and cap rates equalled risk-free returns.