, etc. to get to that sweet spot in the leverage math that makes sense. 

(a real opportunity sweet spot in my RE career).

VRBO used to be a sweet deal. $299/year, for a place on their website.

Quote from @CJ Wine: You can recoupe that money with the over-market rent you should receive, but if you choose not to renew after 3 years and want to rent/sell as a standard SFH, you then have to tear the walls and such back down and now have a bunch of furnishings you probably need to get rid of.Why would you have to tear down the walls and other additions?  

Imagine this on a large scale where people depreciate $10Million  the government gives them a 30 year, zero percent $2.5Million loan  pretty sweet eh?

I am looking into offering wine storage in my facility.  

Chart that out over increasing property values, you'll find a sweet spot that will be about twice of what you are considering for most midwest markets (certainly for Milwaukee).

Depending on the property and location I will do STR but my sweet spot is Long Term Rental.

My loan rate is at 3% which is pretty sweet, but still doesn't help enough with the cashflow situation.

For example if local rents are $3k/mo and your house hack in $1k in the red, thats a sweet deal.