For years, my one bedroom unit did very well on VRBO but once their family / extended family marketing strategy began to kick in, the viewings, inquiries and bookings for this unit took a dive, almost overnight.

Are you saying it could be smart to just extend current lease structure until the spring? 

Ideally, I'd like to have enough to cover an insurance claim and a few thousand extra for turn-over, cap-ex or extended vacancy.

The important thing is to not let these frustrations discourage you from buying a home; in the long run things tends to work out if you don't over-extend yourself and keep a level head. 

You might think you're about to liquidate an asset at foreclosure sale when the borrower files Ch 13 BK on you and extends your timeline out by 5 years. 

I seem to understand the differences between the two in a general rental agreement; “additional interested”=proof that insurance is obtained, changed or cancelled, while “additional insured”extends the policy to me in case of any claims, which will be covered under the renter’s policy first.

I remember in 2015 people were calling the top of the stock market and a good friend of mine who is a portfolio manager moved a lot of his funds to low duration bonds waiting out the pending crash....The market is up 101% in the past 5 years.

Credit extended to acquire, improve, or maintain rental property (regardless of the number of housing units) that is not owner-occupied is deemed to be for business purposes.

Our lender was unresponsive, made many mistakes and ultimately resulted in our closing period getting extended about a month.

It took me a year but I lived there for the duration.