I was quoted for a secondary house mortgage (vacation house), and it was not a DSCR loan. there was no pre-payment penalties. sorry about that!! 

I would appreciate it if you could let me know if you come across anything.I did this for five years and found a hoarder house, the house of a deceased woman that the family wanted to sell discreetly, a vacation rental in a desirable location, a six-plex, an 11-plex, an office, and a nice golf-course home.

Are people really having to give $10k for cash for keys for a tenant to vacate a property in the city of Chicago?

My advice, if you want to invest in STRs, is to go to vacation destinations, think National Parks, beach towns, etc, where the laws are STR friendly.

Currently I’ve been looking at Destin West Vacations.

18-22% management fee is common in Florida for vacation rentals.

Here is my scenario:Sell current LTR; 1031 into Lake STR; rent out for 2-5 years; use personally less than 14 days per year; convert the property to a secondary/vacation residence for my family.

I also ask them for the forwarding address when they give notice that they are vacating the address and also give them a reminder notice of their right to be present at the close out inspection and ask them to tell me when the property will be completely vacant and a request of a date and time to have that inspection if they desire to be present. 

I think my insurance broker (AAA) was able to rig it somehow that one is considered my primary residence and the second a vacation home.

If it is to have a vacation home that someone else helps pay for then maybe.