I'm currently becoming paralyzed by all the analysis and wondering if now is a good time to pull the trigger or wait to see what happens in 2021.

Please do not post "you should seek a tax professional"  I will do this but wanted to know if anyone here knew anything besides "You should seek a tax professional"  Now that we got that out of the way, I want to know if the property is in my name can I move this into a trust without triggering a sale or depreciation recapture? 

After 4 years of massively rising protectionism triggered by a 74 year old leader we now start into a time of slightly less protectionism by a 78 year old leader.

I almost pulled the trigger on turning a couple of our LTR into a short term rental in the past but self managing was what gave me cold feet.

I am using a GC who I know which may be slightly different than your situation but for my deal I know the area and zoning so I was able to calculate and pull the trigger on the deal.Feel free for DM me and I can try to see how I can help you. 

I am currently out of work with a injury and I found a freshly renovated duplex.

Plan on a lower appraisal, say 5-10k less and if those numbers work for you then pull the trigger on the refinance. 

What I mean is, it's great to look at all the pros, cons, numbers, and spreadsheets, but at some point, I want you to pull that trigger and take a leap.

A recent 'get fundable' seminar cautioned about using several "denial trigger words" in your LLC name...words that would get flagged/denied by commercial lending 'automatic approval' software. 

Congrats on pulling the trigger on getting your license.