Commercial normally has a balloon, shorter term and higher interest but no seasoning. 

A lot of things affect this in the shorter term, for instance if it is a well-built newer property, or has just been through a solid renovation, expenses should be lower for a period of time...maybe 30-35% of income. 

If you could go back, what would you have done differently to make your time in between properties shorter and more efficient to purchasing your next? 

You can make it shorter with a lot of risk and leverage, but again, IMO, nothing good comes easy (nor fast).

I can tell you from hundreds of my clients perspective.they don't want to have the burden and work that goes into being a landlord.. they want mail box money and more passive investment that is secured by the same asset that a landlord owns.. there is a reason those banks have those big shinny buildings.. its massively profitable and done right less risk in many cases of being a landlord or at least let me say a ton less work.. your not dealing with the day to day.. even if you have PM you have to manage them.My note buyers are almost all experienced landlords and as their days of landlord burn out come to fruition they switch to being the bank.. keep in mind unless the house is sold for cash.. everyone buying a rental has two steps  equity and debt  IE their equity and the bank or  lenders debt.Along with shorter term holds.. and if done right no cash calls.

Slow selling season with minimal buyers on the island.FRankNice - just be careful with those shorter term fixed rate loans.

But there could always be specific circumstances where a shorter (or longer) hold period are appropriate.In your case an unsolicited offer to buy at an advantageous price would certainly provide a great defense if ever questioned. 

To try to make a long answer to a shorter answer I'll try to make my point. 

At this point I like the idea of shorter term loans with downpayment of at least 20% and 8-8.5%. 

There are several techniques but ones related to your question:1) Doing a Lease Option with the seller gives you equitable interest in the property and you can market the property for sale or for a Lease Option for a period of time shorter than your Option.