My main focus is understanding motels and their operational dynamics.If you’ve invested in or operated a property like this, I’d love to hear from you.

Example: owner bought $1 million SFH in San Francisco as primary, built 400 sq fit ADU, lives in ADU is making gross rental income STR  renting out two levels of main house, grosses $13,000 month.

Mainly because of being priced out of the market around us here in NY.  

But that also depends on your down payment- putting only around 20-25% down is hard to have a profitable STVR.Ultimately with STR v LTR, I'd be mainly curious about your intended use of the property. 

I’ve received multiple quotes from insurance companies (mainly I would obtain the quotes myself).

Once that happens you are in a different world.So I would get rid of the tenant, mainly because there have been 4 violations with the county your tenant has been served.

there was a group of 8 of us that pooled money in a Cabal myself and one other were the main money guys the others put in smaller amounts and when we won one.. we would divy up interest prorata to the amount contributed.. this kept those guys from competing against us and for sure we bid up newbies .. really the only ones that would beat us were those that wanted to live in the house and would just go almost all the way to retail or above .. or someone bidding on a second thinking it was a first and no one is going to help you if you dont know what your doing.. this is a very caveat emptar bizz.

We also have a bank account at a smaller Chicago community bank, but there technology isn't as good to be honest.I think @Jonathan Greene's main point is don't step over dollars to pick up pennies. 

Myself on my own and working with my dad we flipped everything we only bought props with substantial equity that we could resell As fast as possible with my dads company doing mainly wraps as dispo on short term notes .. so the sellers were out of the deals with in 24 to 36 months..

Like @Russell Brazil said there are general things that need to be in place.One that stings a lot of people is the main entrance door.