This is the first home that I am landlording and the first tenant was amazing, I was sad to see her leave but happy because of the reason she left was a good one.I am looking for advice from you seasoned pros! 

I want to ask ya'll seasoned investors if you were starting out today where would you start investing with all the experience and knowledge you have now?

Selling slower here too--FL you have a lot going on--midwest has a seasonality effect. 

This is advantageous bc later you have a third party loan (not your personal money) so seasoning period is 90 days to DSCR out. 

Not every STR has to be a 4 Seasons and even those I've waited on service before and it's not like someone was breathing down their neck waiting to revoke their hotel license when it happened. 

You will not have the rate long enough for it to interfere with your current and proposed profits.This is where having a good team comes into play for example having a seasoned realtor who knows the market on the purchase/ARV side.

The ownership could be changed prior to structuring the parking arrangement, but last-minute changes without time to season the ownership change would significantly increase the risk the transaction could be disallowed as a step transaction under audit.

Now if you are seasoned and portfolio is mature and you are not as concern about maximizing income then I can see a migration to SFH might suit someone.  

While it will likely give you more confidence and answer a lot of questions, I would say that talking to a seasoned investor, or even agent that works with investors, is a way better idea than spending 8K on something that you don't know too much about, especially before your first deal is done.

Other than comps for 3-unit properties (which are typically not furnished and operating as STRs), how would most seasoned STR investors look at valuing the property?