I decided to pull the trigger after a few years of listening to this podcast and reading up on posts in this forum.

I have done it several times now and have also tried long-term rentals vs. short-term rentals as I've house hacked.My response to your question may differ from others, but my advice would be to pull the trigger on the condo if:1. 

But this is the bread and butter of what I do in Detroit.Pay cash, do the renovations, then refi out.As you mentioned, you need to be confident in your comps so you can put an accurate ARV on the project before you pull the trigger. 

Driving for dollars is a very time-consuming task and even if you target distress properties that its only one layer of motivation which for us is not the one that triggers our sellers to be motivated.  

I figured that this might trigger a Change in Accounting method.  

Our plan is to hold long term (10+ years) and likely pay it off in 5-10 years to act as supplemental retirement income which we plan to get to with a couple more properties paid-off in Tulsa eventually.Would you pull the trigger on these two properties based on our goals?

We found a property that we like a lot and was getting ready to pull the trigger on it but wanted to know what would be the best strategy for us without going the conventional loan way or FHA way due to having to; 1-having to put down 20% for conventional and 2-having to live in the property for a minimum of 1 year with the FHA.

If a property is transferred to an LLC, would that trigger a new appraisal for property tax?

Note that if you are 55 in an 401K and leave work, you can access those funds.I know folks that have pulled the trigger and just taken it all out. 

If they are a dentist, chiropractor, electrician, baker, hair salon or anything that requires a building, buy and sell or lease to them.